| Midlands Alliance | ||||
| Date | Home | H | A | Away |
| 11/05/2000 | Rushall Olympic | 1 | 0 | Chasetown |
| 06/05/2000 | Bloxwich Town (R) | 1 | 0 | Rushall Olympic |
| 06/05/2000 | Chasetown | 1 | 1 | Cradley Town (P) |
| 06/05/2000 | Pershore Town | 3 | 3 | Oadby Town (P) |
| 06/05/2000 | Stourport Swifts | 0 | 2 | Willenhall Town |
| 06/05/2000 | Stratford Town | 2 | 1 | Bridgnorth |
| 06/05/2000 | Wednesfield | 3 | 1 | West Midlands Police |
| 04/05/2000 | Knypersley Victoria (-1) | 1 | 0 | Stratford Town |
| 04/05/2000 | West Midlands Police | 0 | 3 | Boldmere St Michaels |
| 03/05/2000 | Bridgnorth | 3 | 2 | Chasetown |
| 02/05/2000 | Oldbury United | 0 | 1 | Chasetown |
| 01/05/2000 | Bloxwich Town (R) | 1 | 1 | Sandwell Borough |
| 01/05/2000 | Bridgnorth | 1 | 1 | Barwell |
| 01/05/2000 | Chasetown | 2 | 0 | Shifnal Town |
| 01/05/2000 | Halesowen Harriers | 2 | 1 | Wednesfield |
| 01/05/2000 | Knypersley Victoria (-1) | 0 | 3 | Stourport Swifts |
| 01/05/2000 | Pershore Town | 0 | 1 | Stapenhill |
| 01/05/2000 | Stratford Town | 3 | 0 | Cradley Town (P) |
| 01/05/2000 | Willenhall Town | 2 | 2 | West Midlands Police |
| 29/04/2000 | Boldmere St Michaels | 1 | 1 | Shifnal Town |
| 29/04/2000 | Chasetown | 2 | 0 | Pershore Town |
| 29/04/2000 | Cradley Town (P) | 0 | 1 | Bloxwich Town (R) |
| 29/04/2000 | Halesowen Harriers | 0 | 3 | Oadby Town (P) |
| 29/04/2000 | Sandwell Borough | 2 | 4 | Willenhall Town |
| 29/04/2000 | Stapenhill | 0 | 3 | Stratford Town |
| 29/04/2000 | Wednesfield | 0 | 1 | Oldbury United |
| 29/04/2000 | West Midlands Police | 2 | 4 | Stourport Swifts |
| 26/04/2000 | Chasetown | 0 | 2 | Stratford Town |
| 24/04/2000 | Barwell | 3 | 2 | Cradley Town (P) |
| 24/04/2000 | Chasetown | 1 | 3 | Stourport Swifts |
| 24/04/2000 | Halesowen Harriers | 2 | 0 | Boldmere St Michaels |
| 24/04/2000 | Kings Norton Town | 2 | 2 | Sandwell Borough |
| 24/04/2000 | Oadby Town (P) | 4 | 1 | Stapenhill |
| 24/04/2000 | Oldbury United | 1 | 3 | Knypersley Victoria (-1) |
| 24/04/2000 | Pelsall Villa | 2 | 1 | Rushall Olympic |
| 24/04/2000 | Shifnal Town | 2 | 0 | Bridgnorth |
| 24/04/2000 | Stratford Town | 0 | 2 | Pershore Town |
| 24/04/2000 | Willenhall Town | 2 | 2 | Wednesfield |
| 22/04/2000 | Barwell | 2 | 0 | Pershore Town |
| 22/04/2000 | Bridgnorth | 1 | 1 | Stratford Town |
| 22/04/2000 | Halesowen Harriers | 3 | 1 | Pelsall Villa |
| 22/04/2000 | Kings Norton Town | 2 | 1 | Wednesfield |
| 22/04/2000 | Oadby Town (P) | 2 | 0 | Knypersley Victoria (-1) |
| 22/04/2000 | Rushall Olympic | 2 | 1 | Willenhall Town |
| 22/04/2000 | Stourport Swifts | 2 | 4 | Boldmere St Michaels |
| 22/04/2000 | West Midlands Police | 0 | 1 | Shifnal Town |
| 19/04/2000 | Oadby Town (P) | 2 | 1 | Chasetown |
| 19/04/2000 | Pelsall Villa | 3 | 2 | Oldbury United |
| 18/04/2000 | Knypersley Victoria (-1) | 1 | 3 | Halesowen Harriers |
| 15/04/2000 | Boldmere St Michaels | 2 | 1 | Oadby Town (P) |
| 15/04/2000 | Chasetown | 4 | 1 | Bloxwich Town (R) |
| 15/04/2000 | Cradley Town (P) | 2 | 2 | Knypersley Victoria (-1) |
| 15/04/2000 | Oldbury United | 3 | 1 | West Midlands Police |
| 15/04/2000 | Pelsall Villa | 1 | 4 | Kings Norton Town |
| 15/04/2000 | Pershore Town | 2 | 5 | Barwell |
| 15/04/2000 | Sandwell Borough | 1 | 2 | Rushall Olympic |
| 15/04/2000 | Shifnal Town | 0 | 0 | Halesowen Harriers |
| 15/04/2000 | Stapenhill | 0 | 3 | Bridgnorth |
| 15/04/2000 | Stratford Town | 3 | 2 | Willenhall Town |
| 15/04/2000 | Wednesfield | 3 | 1 | Stourport Swifts |
| 11/04/2000 | Barwell | 2 | 0 | West Midlands Police |
| 11/04/2000 | Knypersley Victoria (-1) | 1 | 1 | Chasetown |
| 11/04/2000 | Willenhall Town | 2 | 1 | Bridgnorth |
| 08/04/2000 | Barwell | 4 | 1 | Shifnal Town |
| 08/04/2000 | Bloxwich Town (R) | 3 | 0 | Pelsall Villa |
| 08/04/2000 | Bridgnorth | 3 | 0 | Cradley Town (P) |
| 08/04/2000 | Chasetown | 3 | 0 | Wednesfield |
| 08/04/2000 | Halesowen Harriers | 0 | 1 | Oldbury United |
| 08/04/2000 | Pershore Town | 0 | 1 | Boldmere St Michaels |
| 08/04/2000 | Rushall Olympic | 2 | 2 | Stratford Town |
| 08/04/2000 | Sandwell Borough | 0 | 1 | Oadby Town (P) |
| 08/04/2000 | Stourport Swifts | 2 | 2 | Knypersley Victoria (-1) |
| 08/04/2000 | West Midlands Police | 0 | 0 | Kings Norton Town |
| 08/04/2000 | Willenhall Town | 1 | 0 | Stapenhill |
| 04/04/2000 | Rushall Olympic | 3 | 2 | Sandwell Borough |
| 04/04/2000 | West Midlands Police | 1 | 3 | Oldbury United |
| 01/04/2000 | Boldmere St Michaels | 0 | 0 | Stratford Town |
| 01/04/2000 | Cradley Town (P) | 0 | 0 | Sandwell Borough |
| 01/04/2000 | Halesowen Harriers | 0 | 1 | Chasetown |
| 01/04/2000 | Kings Norton Town | 2 | 2 | Stourport Swifts |
| 01/04/2000 | Knypersley Victoria (-1) | 1 | 2 | Willenhall Town |
| 01/04/2000 | Oadby Town (P) | 2 | 1 | Bridgnorth |
| 01/04/2000 | Oldbury United | 0 | 0 | Barwell |
| 01/04/2000 | Shifnal Town | 1 | 0 | Pershore Town |
| 01/04/2000 | Stapenhill | 0 | 2 | Rushall Olympic |
| 01/04/2000 | Wednesfield | 0 | 0 | Bloxwich Town (R) |
| 28/03/2000 | Kings Norton Town | 4 | 0 | Pelsall Villa |
| 28/03/2000 | Stratford Town | 1 | 0 | Stourport Swifts |
| 28/03/2000 | Wednesfield | 1 | 0 | Chasetown |
| 25/03/2000 | Barwell | 4 | 1 | Chasetown |
| 25/03/2000 | Bloxwich Town (R) | 2 | 3 | Kings Norton Town |
| 25/03/2000 | Bridgnorth | 1 | 1 | Oldbury United |
| 25/03/2000 | Knypersley Victoria (-1) | 1 | 1 | Boldmere St Michaels |
| 25/03/2000 | Pershore Town | 2 | 5 | Wednesfield |
| 25/03/2000 | Rushall Olympic | 1 | 0 | Cradley Town (P) |
| 25/03/2000 | Sandwell Borough | 3 | 1 | Stapenhill |
| 25/03/2000 | Stourport Swifts | 3 | 2 | Pelsall Villa |
| 25/03/2000 | Stratford Town | 0 | 3 | Shifnal Town |
| 25/03/2000 | West Midlands Police | 2 | 1 | Halesowen Harriers |
| 25/03/2000 | Willenhall Town | 0 | 3 | Oadby Town (P) |
| 21/03/2000 | Pelsall Villa | 3 | 2 | Halesowen Harriers |
| 21/03/2000 | West Midlands Police | 2 | 1 | Barwell |
| 18/03/2000 | Barwell | 1 | 5 | Oadby Town (P) |
| 18/03/2000 | Boldmere St Michaels | 0 | 3 | Rushall Olympic |
| 18/03/2000 | Chasetown | 0 | 3 | Knypersley Victoria (-1) |
| 18/03/2000 | Cradley Town (P) | 0 | 6 | Willenhall Town |
| 18/03/2000 | Halesowen Harriers | 0 | 3 | Stourport Swifts |
| 18/03/2000 | Kings Norton Town | 0 | 3 | Bridgnorth |
| 18/03/2000 | Oldbury United | 1 | 1 | Stratford Town |
| 18/03/2000 | Pelsall Villa | 3 | 0 | Pershore Town |
| 18/03/2000 | Shifnal Town | 1 | 1 | Sandwell Borough |
| 18/03/2000 | Wednesfield | 2 | 1 | Stapenhill |
| 15/03/2000 | Bloxwich Town (R) | 5 | 0 | Chasetown |
| 14/03/2000 | Barwell | 0 | 1 | Willenhall Town |
| 14/03/2000 | Bridgnorth | 4 | 1 | Stapenhill |
| 14/03/2000 | Halesowen Harriers | 2 | 2 | Shifnal Town |
| 14/03/2000 | Pershore Town | 0 | 0 | Stourport Swifts |
| 11/03/2000 | Bridgnorth | 2 | 3 | West Midlands Police |
| 11/03/2000 | Cradley Town (P) | 1 | 6 | Oadby Town (P) |
| 11/03/2000 | Knypersley Victoria (-1) | 0 | 4 | Pelsall Villa |
| 11/03/2000 | Pershore Town | 0 | 3 | Kings Norton Town |
| 11/03/2000 | Rushall Olympic | 1 | 1 | Shifnal Town |
| 11/03/2000 | Sandwell Borough | 3 | 2 | Chasetown |
| 11/03/2000 | Stapenhill | 4 | 2 | Oldbury United |
| 11/03/2000 | Stourport Swifts | 2 | 1 | Bloxwich Town (R) |
| 11/03/2000 | Stratford Town | 0 | 1 | Halesowen Harriers |
| 11/03/2000 | Willenhall Town | 1 | 1 | Boldmere St Michaels |
| 07/03/2000 | Boldmere St Michaels | 1 | 0 | Pelsall Villa |
| 07/03/2000 | Halesowen Harriers | 4 | 1 | Kings Norton Town |
| 07/03/2000 | Rushall Olympic | 0 | 3 | Knypersley Victoria (-1) |
| 07/03/2000 | Sandwell Borough | 0 | 5 | Stratford Town |
| 07/03/2000 | Shifnal Town | 0 | 0 | Cradley Town (P) |
| 07/03/2000 | West Midlands Police | 1 | 0 | Stapenhill |
| 04/03/2000 | Bloxwich Town (R) | 3 | 2 | Pershore Town |
| 04/03/2000 | Boldmere St Michaels | 3 | 2 | Cradley Town (P) |
| 04/03/2000 | Chasetown | 1 | 4 | Willenhall Town |
| 04/03/2000 | Halesowen Harriers | 0 | 2 | Sandwell Borough |
| 04/03/2000 | Oldbury United | 0 | 0 | Oadby Town (P) |
| 04/03/2000 | Pelsall Villa | 1 | 3 | Bridgnorth |
| 04/03/2000 | Shifnal Town | 3 | 3 | Stapenhill |
| 04/03/2000 | Stourport Swifts | 1 | 4 | Barwell |
| 04/03/2000 | Wednesfield | 0 | 2 | Stratford Town |
| 04/03/2000 | West Midlands Police | 1 | 0 | Rushall Olympic |
| 01/03/2000 | Kings Norton Town | 2 | 2 | Chasetown |
| 26/02/2000 | Barwell | 6 | 2 | Pelsall Villa |
| 26/02/2000 | Bridgnorth | 2 | 3 | Bloxwich Town (R) |
| 26/02/2000 | Cradley Town (P) | 1 | 3 | Stourport Swifts |
| 26/02/2000 | Knypersley Victoria (-1) | 1 | 1 | West Midlands Police |
| 26/02/2000 | Oadby Town (P) | 1 | 1 | Halesowen Harriers |
| 26/02/2000 | Pershore Town | 0 | 0 | Oldbury United |
| 26/02/2000 | Rushall Olympic | 0 | 2 | Wednesfield |
| 26/02/2000 | Sandwell Borough | 0 | 0 | Boldmere St Michaels |
| 26/02/2000 | Stapenhill | 1 | 0 | Chasetown |
| 26/02/2000 | Stratford Town | 0 | 1 | Kings Norton Town |
| 26/02/2000 | Willenhall Town | 3 | 0 | Shifnal Town |
| 22/02/2000 | Knypersley Victoria (-1) | 1 | 0 | Barwell |
| 22/02/2000 | Oldbury United | 1 | 0 | Boldmere St Michaels |
| 19/02/2000 | Bloxwich Town (R) | 4 | 1 | Stapenhill |
| 19/02/2000 | Boldmere St Michaels | 0 | 1 | Bridgnorth |
| 19/02/2000 | Halesowen Harriers | 2 | 0 | Barwell |
| 19/02/2000 | Kings Norton Town | 1 | 1 | Willenhall Town |
| 19/02/2000 | Oldbury United | 1 | 1 | Sandwell Borough |
| 19/02/2000 | Pelsall Villa | 1 | 1 | Stratford Town |
| 19/02/2000 | Shifnal Town | 2 | 0 | Oadby Town (P) |
| 19/02/2000 | Stourport Swifts | 2 | 2 | Rushall Olympic |
| 19/02/2000 | Wednesfield | 5 | 3 | Knypersley Victoria (-1) |
| 19/02/2000 | West Midlands Police | 4 | 2 | Pershore Town |
| 16/02/2000 | Oadby Town (P) | 3 | 1 | Boldmere St Michaels |
| 16/02/2000 | Pelsall Villa | 1 | 1 | Shifnal Town |
| 15/02/2000 | Oldbury United | 0 | 2 | Wednesfield |
| 15/02/2000 | Sandwell Borough | 3 | 0 | West Midlands Police |
| 15/02/2000 | Stourport Swifts | 3 | 1 | Stapenhill |
| 15/02/2000 | Willenhall Town | 0 | 1 | Stratford Town |
| 12/02/2000 | Barwell | 2 | 2 | Boldmere St Michaels |
| 12/02/2000 | Cradley Town (P) | 1 | 1 | Kings Norton Town |
| 12/02/2000 | Knypersley Victoria (-1) | 3 | 1 | Pershore Town |
| 12/02/2000 | Oadby Town (P) | 1 | 4 | Wednesfield |
| 12/02/2000 | Rushall Olympic | 0 | 1 | Oldbury United |
| 12/02/2000 | Shifnal Town | 1 | 0 | Stourport Swifts |
| 12/02/2000 | Stapenhill | 1 | 1 | Pelsall Villa |
| 12/02/2000 | Stratford Town | 3 | 2 | Bloxwich Town (R) |
| 12/02/2000 | Willenhall Town | 1 | 1 | Halesowen Harriers |
| 09/02/2000 | Bloxwich Town (R) | 2 | 2 | Shifnal Town |
| 09/02/2000 | Pelsall Villa | 1 | 1 | Chasetown |
| 08/02/2000 | Bridgnorth | 4 | 2 | Knypersley Victoria (-1) |
| 08/02/2000 | Kings Norton Town | 0 | 2 | Oadby Town (P) |
| 08/02/2000 | Pershore Town | 1 | 3 | Willenhall Town |
| 08/02/2000 | Stapenhill | 0 | 0 | Barwell |
| 08/02/2000 | Stourport Swifts | 2 | 3 | Sandwell Borough |
| 08/02/2000 | Wednesfield | 2 | 0 | Cradley Town (P) |
| 08/02/2000 | West Midlands Police | 6 | 2 | Stratford Town |
| 05/02/2000 | Barwell | 1 | 0 | Kings Norton Town |
| 05/02/2000 | Boldmere St Michaels | 4 | 2 | Wednesfield |
| 05/02/2000 | Knypersley Victoria (-1) | 3 | 1 | Bloxwich Town (R) |
| 05/02/2000 | Oadby Town (P) | 1 | 2 | Stourport Swifts |
| 05/02/2000 | Rushall Olympic | 2 | 0 | Bridgnorth |
| 05/02/2000 | Sandwell Borough | 2 | 3 | Pershore Town |
| 05/02/2000 | Stapenhill | 4 | 3 | Halesowen Harriers |
| 05/02/2000 | West Midlands Police | 2 | 2 | Cradley Town (P) |
| 05/02/2000 | Willenhall Town | 1 | 2 | Pelsall Villa |
| 01/02/2000 | Kings Norton Town | 0 | 2 | Rushall Olympic |
| 29/01/2000 | Bloxwich Town (R) | 0 | 3 | Barwell |
| 29/01/2000 | Bridgnorth | 1 | 2 | Pershore Town |
| 29/01/2000 | Kings Norton Town | 4 | 1 | Shifnal Town |
| 29/01/2000 | Oldbury United | 1 | 2 | Cradley Town (P) |
| 29/01/2000 | Pelsall Villa | 1 | 3 | West Midlands Police |
| 29/01/2000 | Rushall Olympic | 1 | 4 | Oadby Town (P) |
| 29/01/2000 | Wednesfield | 2 | 1 | Sandwell Borough |
| 26/01/2000 | Oadby Town (P) | 3 | 1 | Stratford Town |
| 25/01/2000 | Boldmere St Michaels | 0 | 0 | Bloxwich Town (R) |
| 25/01/2000 | Sandwell Borough | 2 | 0 | Pelsall Villa |
| 25/01/2000 | Shifnal Town | 1 | 0 | Knypersley Victoria (-1) |
| 25/01/2000 | Stapenhill | 1 | 1 | Kings Norton Town |
| 25/01/2000 | Stourport Swifts | 1 | 3 | Bridgnorth |
| 25/01/2000 | West Midlands Police | 0 | 1 | Chasetown |
| 25/01/2000 | Willenhall Town | 2 | 2 | Oldbury United |
| 22/01/2000 | Bloxwich Town (R) | 1 | 2 | Willenhall Town |
| 22/01/2000 | Bridgnorth | 0 | 3 | Halesowen Harriers |
| 22/01/2000 | Knypersley Victoria (-1) | 2 | 1 | Sandwell Borough |
| 22/01/2000 | Oldbury United | 2 | 0 | Stourport Swifts |
| 22/01/2000 | Pelsall Villa | 1 | 4 | Cradley Town (P) |
| 22/01/2000 | Pershore Town | 2 | 2 | Rushall Olympic |
| 22/01/2000 | Stapenhill | 0 | 1 | Boldmere St Michaels |
| 22/01/2000 | Stratford Town | 2 | 2 | Barwell |
| 22/01/2000 | Wednesfield | 0 | 1 | Shifnal Town |
| 22/01/2000 | West Midlands Police | 0 | 3 | Oadby Town (P) |
| 18/01/2000 | Shifnal Town | 0 | 0 | Chasetown |
| 18/01/2000 | Stourport Swifts | 3 | 2 | Halesowen Harriers |
| 18/01/2000 | Stratford Town | 0 | 0 | Oldbury United |
| 15/01/2000 | Boldmere St Michaels | 3 | 1 | Kings Norton Town |
| 15/01/2000 | Cradley Town (P) | 2 | 2 | Barwell |
| 15/01/2000 | Halesowen Harriers | 0 | 1 | Knypersley Victoria (-1) |
| 15/01/2000 | Oadby Town (P) | 3 | 0 | Rushall Olympic |
| 15/01/2000 | Pelsall Villa | 1 | 2 | Wednesfield |
| 15/01/2000 | Sandwell Borough | 2 | 1 | Bridgnorth |
| 15/01/2000 | Shifnal Town | 1 | 5 | Oldbury United |
| 15/01/2000 | Stratford Town | 1 | 0 | Stapenhill |
| 15/01/2000 | West Midlands Police | 5 | 2 | Bloxwich Town (R) |
| 15/01/2000 | Willenhall Town | 1 | 1 | Stourport Swifts |
| 11/01/2000 | Bridgnorth | 1 | 1 | Willenhall Town |
| 11/01/2000 | Kings Norton Town | 0 | 1 | West Midlands Police |
| 11/01/2000 | Pershore Town | 3 | 0 | Halesowen Harriers |
| 08/01/2000 | Barwell | 2 | 1 | Bridgnorth |
| 08/01/2000 | Boldmere St Michaels | 2 | 1 | Halesowen Harriers |
| 08/01/2000 | Cradley Town (P) | 0 | 1 | Stratford Town |
| 08/01/2000 | Kings Norton Town | 1 | 4 | Oldbury United |
| 08/01/2000 | Knypersley Victoria (-1) | 0 | 4 | Oadby Town (P) |
| 08/01/2000 | Rushall Olympic | 2 | 2 | Bloxwich Town (R) |
| 08/01/2000 | Shifnal Town | 3 | 2 | Pelsall Villa |
| 08/01/2000 | Stapenhill | 4 | 1 | Pershore Town |
| 08/01/2000 | Stourport Swifts | 1 | 1 | Chasetown |
| 08/01/2000 | West Midlands Police | 4 | 0 | Wednesfield |
| 08/01/2000 | Willenhall Town | 0 | 0 | Sandwell Borough |
| 27/12/1999 | Bridgnorth | 0 | 6 | Shifnal Town |
| 27/12/1999 | Chasetown | 3 | 1 | Boldmere St Michaels |
| 27/12/1999 | Halesowen Harriers | 2 | 2 | Cradley Town (P) |
| 27/12/1999 | Oadby Town (P) | 2 | 1 | Barwell |
| 27/12/1999 | Oldbury United | 2 | 0 | Bloxwich Town (R) |
| 27/12/1999 | Pershore Town | 1 | 2 | Stratford Town |
| 27/12/1999 | Rushall Olympic | 2 | 2 | Pelsall Villa |
| 27/12/1999 | Sandwell Borough | 1 | 1 | Kings Norton Town |
| 27/12/1999 | Stapenhill | 3 | 2 | Knypersley Victoria (-1) |
| 27/12/1999 | Stourport Swifts | 2 | 2 | West Midlands Police |
| 27/12/1999 | Wednesfield | 2 | 3 | Willenhall Town |
| 18/12/1999 | Bloxwich Town (R) | 0 | 7 | Oadby Town (P) |
| 18/12/1999 | Boldmere St Michaels | 1 | 1 | Stourport Swifts |
| 18/12/1999 | Chasetown | 3 | 1 | Oldbury United |
| 18/12/1999 | Cradley Town (P) | 2 | 1 | Stapenhill |
| 18/12/1999 | Pershore Town | 2 | 3 | Bridgnorth |
| 18/12/1999 | Sandwell Borough | 2 | 2 | Barwell |
| 18/12/1999 | Shifnal Town | 2 | 1 | West Midlands Police |
| 18/12/1999 | Stratford Town | 4 | 1 | Knypersley Victoria (-1) |
| 18/12/1999 | Wednesfield | 2 | 1 | Kings Norton Town |
| 18/12/1999 | Willenhall Town | 1 | 2 | Rushall Olympic |
| 11/12/1999 | Knypersley Victoria (-1) | 8 | 1 | Cradley Town (P) |
| 11/12/1999 | Stourport Swifts | 0 | 0 | Wednesfield |
| 07/12/1999 | Chasetown | 3 | 1 | Rushall Olympic |
| 04/12/1999 | Boldmere St Michaels | 3 | 2 | Pershore Town |
| 04/12/1999 | Cradley Town (P) | 4 | 2 | Bridgnorth |
| 04/12/1999 | Kings Norton Town | 1 | 1 | Knypersley Victoria (-1) |
| 04/12/1999 | Oadby Town (P) | 3 | 1 | Sandwell Borough |
| 04/12/1999 | Oldbury United | 3 | 0 | Halesowen Harriers |
| 04/12/1999 | Pelsall Villa | 3 | 1 | Bloxwich Town (R) |
| 04/12/1999 | Shifnal Town | 2 | 0 | Barwell |
| 04/12/1999 | Stapenhill | 0 | 3 | Willenhall Town |
| 04/12/1999 | Stratford Town | 5 | 0 | Rushall Olympic |
| 30/11/1999 | Sandwell Borough | 0 | 3 | Shifnal Town |
| 27/11/1999 | Barwell | 1 | 0 | Oldbury United |
| 27/11/1999 | Bloxwich Town (R) | 1 | 1 | Wednesfield |
| 27/11/1999 | Bridgnorth | 3 | 2 | Oadby Town (P) |
| 27/11/1999 | Chasetown | 1 | 2 | Halesowen Harriers |
| 27/11/1999 | Pershore Town | 0 | 3 | Shifnal Town |
| 27/11/1999 | Rushall Olympic | 3 | 2 | Stapenhill |
| 27/11/1999 | Sandwell Borough | 1 | 3 | Cradley Town (P) |
| 27/11/1999 | Stourport Swifts | 3 | 1 | Kings Norton Town |
| 27/11/1999 | Stratford Town | 2 | 2 | Boldmere St Michaels |
| 27/11/1999 | West Midlands Police | 2 | 0 | Pelsall Villa |
| 27/11/1999 | Willenhall Town | 0 | 2 | Knypersley Victoria (-1) |
| 24/11/1999 | Oadby Town (P) | 0 | 3 | Shifnal Town |
| 20/11/1999 | Boldmere St Michaels | 4 | 2 | Knypersley Victoria (-1) |
| 20/11/1999 | Chasetown | 2 | 1 | Barwell |
| 20/11/1999 | Cradley Town (P) | 2 | 7 | Rushall Olympic |
| 20/11/1999 | Halesowen Harriers | 1 | 3 | West Midlands Police |
| 20/11/1999 | Kings Norton Town | 1 | 1 | Bloxwich Town (R) |
| 20/11/1999 | Oadby Town (P) | 2 | 2 | Willenhall Town |
| 20/11/1999 | Oldbury United | 1 | 1 | Bridgnorth |
| 20/11/1999 | Pelsall Villa | 0 | 2 | Stourport Swifts |
| 20/11/1999 | Shifnal Town | 1 | 1 | Stratford Town |
| 20/11/1999 | Stapenhill | 2 | 0 | Sandwell Borough |
| 20/11/1999 | Wednesfield | 3 | 1 | Pershore Town |
| 13/11/1999 | Bloxwich Town (R) | 1 | 1 | Halesowen Harriers |
| 13/11/1999 | Pershore Town | 2 | 1 | Pelsall Villa |
| 13/11/1999 | Rushall Olympic | 2 | 0 | Boldmere St Michaels |
| 13/11/1999 | Stapenhill | 1 | 2 | Wednesfield |
| 13/11/1999 | Willenhall Town | 0 | 1 | Cradley Town (P) |
| 12/11/1999 | Barwell | 7 | 1 | Sandwell Borough |
| 06/11/1999 | Bridgnorth | 1 | 0 | Kings Norton Town |
| 06/11/1999 | Oldbury United | 4 | 2 | Rushall Olympic |
| 06/11/1999 | Pelsall Villa | 1 | 3 | Oadby Town (P) |
| 02/11/1999 | Barwell | 5 | 0 | Bloxwich Town (R) |
| 30/10/1999 | Bloxwich Town (R) | 0 | 3 | Stourport Swifts |
| 30/10/1999 | Boldmere St Michaels | 1 | 0 | Willenhall Town |
| 30/10/1999 | Chasetown | 2 | 1 | Sandwell Borough |
| 30/10/1999 | Halesowen Harriers | 0 | 2 | Stratford Town |
| 30/10/1999 | Kings Norton Town | 1 | 1 | Pershore Town |
| 30/10/1999 | Oadby Town (P) | 3 | 0 | Cradley Town (P) |
| 30/10/1999 | Oldbury United | 3 | 0 | Stapenhill |
| 30/10/1999 | Pelsall Villa | 1 | 2 | Knypersley Victoria (-1) |
| 30/10/1999 | Shifnal Town | 1 | 0 | Rushall Olympic |
| 30/10/1999 | Wednesfield | 2 | 1 | Barwell |
| 30/10/1999 | West Midlands Police | 3 | 4 | Bridgnorth |
| 23/10/1999 | Barwell | 1 | 2 | Rushall Olympic |
| 23/10/1999 | Cradley Town (P) | 3 | 0 | Pershore Town |
| 23/10/1999 | Halesowen Harriers | 7 | 2 | Bloxwich Town (R) |
| 23/10/1999 | Stapenhill | 0 | 4 | Oadby Town (P) |
| 23/10/1999 | Wednesfield | 0 | 4 | Bridgnorth |
| 19/10/1999 | Chasetown | 1 | 2 | Oadby Town (P) |
| 19/10/1999 | Willenhall Town | 1 | 1 | Barwell |
| 16/10/1999 | Barwell | 1 | 1 | Stourport Swifts |
| 16/10/1999 | Bridgnorth | 5 | 1 | Pelsall Villa |
| 16/10/1999 | Cradley Town (P) | 0 | 3 | Boldmere St Michaels |
| 16/10/1999 | Knypersley Victoria (-1) | 4 | 3 | Kings Norton Town |
| 16/10/1999 | Oadby Town (P) | 0 | 0 | Oldbury United |
| 16/10/1999 | Pershore Town | 2 | 0 | Bloxwich Town (R) |
| 16/10/1999 | Rushall Olympic | 0 | 0 | West Midlands Police |
| 16/10/1999 | Sandwell Borough | 3 | 2 | Halesowen Harriers |
| 16/10/1999 | Stapenhill | 0 | 3 | Shifnal Town |
| 16/10/1999 | Stratford Town | 2 | 1 | Wednesfield |
| 16/10/1999 | Willenhall Town | 1 | 0 | Chasetown |
| 09/10/1999 | Bloxwich Town (R) | 3 | 2 | Bridgnorth |
| 09/10/1999 | Boldmere St Michaels | 1 | 0 | Sandwell Borough |
| 09/10/1999 | Chasetown | 3 | 1 | Stapenhill |
| 09/10/1999 | Halesowen Harriers | 3 | 4 | Rushall Olympic |
| 09/10/1999 | Kings Norton Town | 1 | 2 | Stratford Town |
| 09/10/1999 | Oldbury United | 6 | 0 | Pershore Town |
| 09/10/1999 | Pelsall Villa | 2 | 2 | Barwell |
| 09/10/1999 | Shifnal Town | 1 | 2 | Willenhall Town |
| 09/10/1999 | Stourport Swifts | 3 | 2 | Cradley Town (P) |
| 09/10/1999 | Wednesfield | 1 | 1 | Oadby Town (P) |
| 09/10/1999 | West Midlands Police | 0 | 3 | Knypersley Victoria (-1) |
| 02/10/1999 | Barwell | 0 | 0 | Halesowen Harriers |
| 02/10/1999 | Bridgnorth | 0 | 2 | Boldmere St Michaels |
| 02/10/1999 | Cradley Town (P) | 1 | 3 | Chasetown |
| 02/10/1999 | Knypersley Victoria (-1) | 2 | 0 | Wednesfield |
| 02/10/1999 | Pershore Town | 0 | 2 | West Midlands Police |
| 02/10/1999 | Rushall Olympic | 1 | 2 | Stourport Swifts |
| 02/10/1999 | Sandwell Borough | 1 | 0 | Oldbury United |
| 02/10/1999 | Stapenhill | 2 | 2 | Bloxwich Town (R) |
| 02/10/1999 | Stratford Town | 3 | 1 | Pelsall Villa |
| 02/10/1999 | Willenhall Town | 0 | 0 | Kings Norton Town |
| 28/09/1999 | Shifnal Town | 4 | 4 | Kings Norton Town |
| 25/09/1999 | Barwell | 0 | 0 | Wednesfield |
| 25/09/1999 | Oadby Town (P) | 6 | 2 | Bloxwich Town (R) |
| 25/09/1999 | Oldbury United | 0 | 3 | Kings Norton Town |
| 21/09/1999 | Knypersley Victoria (-1) | 0 | 1 | Oldbury United |
| 21/09/1999 | Stourport Swifts | 0 | 2 | Stratford Town |
| 18/09/1999 | Bloxwich Town (R) | 1 | 1 | Stratford Town |
| 18/09/1999 | Boldmere St Michaels | 2 | 3 | Barwell |
| 18/09/1999 | Chasetown | 2 | 1 | Bridgnorth |
| 18/09/1999 | Halesowen Harriers | 0 | 4 | Willenhall Town |
| 18/09/1999 | Kings Norton Town | 2 | 2 | Cradley Town (P) |
| 18/09/1999 | Pelsall Villa | 1 | 1 | Stapenhill |
| 18/09/1999 | Pershore Town | 3 | 3 | Knypersley Victoria (-1) |
| 18/09/1999 | Stourport Swifts | 1 | 1 | Shifnal Town |
| 18/09/1999 | Wednesfield | 1 | 1 | Rushall Olympic |
| 18/09/1999 | West Midlands Police | 1 | 2 | Sandwell Borough |
| 14/09/1999 | Cradley Town (P) | 1 | 2 | Halesowen Harriers |
| 14/09/1999 | Shifnal Town | 0 | 1 | Boldmere St Michaels |
| 11/09/1999 | Boldmere St Michaels | 1 | 3 | Chasetown |
| 11/09/1999 | Oadby Town (P) | 3 | 0 | Pershore Town |
| 11/09/1999 | Oldbury United | 2 | 2 | Pelsall Villa |
| 11/09/1999 | Rushall Olympic | 2 | 2 | Kings Norton Town |
| 11/09/1999 | Sandwell Borough | 1 | 0 | Bloxwich Town (R) |
| 11/09/1999 | Stapenhill | 1 | 2 | Stourport Swifts |
| 11/09/1999 | West Midlands Police | 0 | 5 | Willenhall Town |
| 08/09/1999 | Bloxwich Town (R) | 2 | 0 | Oldbury United |
| 08/09/1999 | Pelsall Villa | 1 | 2 | Boldmere St Michaels |
| 07/09/1999 | Bridgnorth | 0 | 3 | Wednesfield |
| 07/09/1999 | Cradley Town (P) | 1 | 1 | Shifnal Town |
| 07/09/1999 | Kings Norton Town | 0 | 1 | Halesowen Harriers |
| 07/09/1999 | Knypersley Victoria (-1) | 2 | 5 | Rushall Olympic |
| 07/09/1999 | Stapenhill | 0 | 2 | West Midlands Police |
| 07/09/1999 | Stourport Swifts | 4 | 0 | Pershore Town |
| 07/09/1999 | Stratford Town | 1 | 1 | Sandwell Borough |
| 04/09/1999 | Barwell | 3 | 2 | Knypersley Victoria (-1) |
| 04/09/1999 | Bloxwich Town (R) | 2 | 1 | West Midlands Police |
| 04/09/1999 | Bridgnorth | 1 | 1 | Sandwell Borough |
| 04/09/1999 | Kings Norton Town | 0 | 2 | Boldmere St Michaels |
| 04/09/1999 | Pershore Town | 2 | 1 | Chasetown |
| 04/09/1999 | Stapenhill | 0 | 3 | Cradley Town (P) |
| 04/09/1999 | Wednesfield | 1 | 1 | Pelsall Villa |
| 30/08/1999 | Barwell | 3 | 1 | Stapenhill |
| 30/08/1999 | Boldmere St Michaels | 1 | 1 | Oldbury United |
| 30/08/1999 | Chasetown | 0 | 4 | Pelsall Villa |
| 30/08/1999 | Cradley Town (P) | 1 | 2 | Wednesfield |
| 30/08/1999 | Knypersley Victoria (-1) | 1 | 0 | Bridgnorth |
| 30/08/1999 | Oadby Town (P) | 1 | 1 | Kings Norton Town |
| 30/08/1999 | Rushall Olympic | 2 | 1 | Halesowen Harriers |
| 30/08/1999 | Sandwell Borough | 1 | 1 | Stourport Swifts |
| 30/08/1999 | Shifnal Town | 0 | 1 | Bloxwich Town (R) |
| 30/08/1999 | Stratford Town | 2 | 0 | West Midlands Police |
| 30/08/1999 | Willenhall Town | 7 | 0 | Pershore Town |
| 28/08/1999 | Bloxwich Town (R) | 1 | 1 | Knypersley Victoria (-1) |
| 28/08/1999 | Bridgnorth | 1 | 3 | Rushall Olympic |
| 28/08/1999 | Cradley Town (P) | 1 | 1 | West Midlands Police |
| 28/08/1999 | Halesowen Harriers | 3 | 0 | Stapenhill |
| 28/08/1999 | Kings Norton Town | 3 | 1 | Barwell |
| 28/08/1999 | Oldbury United | 3 | 2 | Shifnal Town |
| 28/08/1999 | Pelsall Villa | 0 | 0 | Willenhall Town |
| 28/08/1999 | Pershore Town | 2 | 3 | Sandwell Borough |
| 28/08/1999 | Stourport Swifts | 3 | 2 | Oadby Town (P) |
| 28/08/1999 | Stratford Town | 1 | 1 | Chasetown |
| 28/08/1999 | Wednesfield | 3 | 0 | Boldmere St Michaels |
| 25/08/1999 | Oadby Town (P) | 5 | 1 | Pelsall Villa |
| 24/08/1999 | Boldmere St Michaels | 1 | 1 | West Midlands Police |
| 24/08/1999 | Cradley Town (P) | 1 | 2 | Oldbury United |
| 24/08/1999 | Halesowen Harriers | 3 | 2 | Pershore Town |
| 24/08/1999 | Knypersley Victoria (-1) | 3 | 0 | Stapenhill |
| 24/08/1999 | Sandwell Borough | 0 | 1 | Wednesfield |
| 21/08/1999 | Bloxwich Town (R) | 2 | 2 | Cradley Town (P) |
| 18/08/1999 | Bloxwich Town (R) | 0 | 0 | Boldmere St Michaels |
| 18/08/1999 | Pelsall Villa | 2 | 0 | Sandwell Borough |
| 17/08/1999 | Bridgnorth | 0 | 1 | Stourport Swifts |
| 17/08/1999 | Chasetown | 2 | 1 | West Midlands Police |
| 17/08/1999 | Kings Norton Town | 1 | 2 | Stapenhill |
| 17/08/1999 | Knypersley Victoria (-1) | 1 | 1 | Shifnal Town |
| 17/08/1999 | Oldbury United | 1 | 2 | Willenhall Town |
| 17/08/1999 | Pershore Town | 0 | 1 | Cradley Town (P) |
| 17/08/1999 | Rushall Olympic | 4 | 2 | Barwell |
| 17/08/1999 | Stratford Town | 6 | 2 | Oadby Town (P) |
| 17/08/1999 | Wednesfield | 4 | 1 | Halesowen Harriers |
| 14/08/1999 | Barwell | 5 | 0 | Stratford Town |
| 14/08/1999 | Boldmere St Michaels | 3 | 0 | Stapenhill |
| 14/08/1999 | Chasetown | 3 | 1 | Kings Norton Town |
| 14/08/1999 | Cradley Town (P) | 2 | 0 | Pelsall Villa |
| 14/08/1999 | Halesowen Harriers | 1 | 1 | Bridgnorth |
| 14/08/1999 | Oadby Town (P) | 2 | 0 | West Midlands Police |
| 14/08/1999 | Rushall Olympic | 3 | 0 | Pershore Town |
| 14/08/1999 | Sandwell Borough | 1 | 1 | Knypersley Victoria (-1) |
| 14/08/1999 | Shifnal Town | 3 | 3 | Wednesfield |
| 14/08/1999 | Stourport Swifts | 0 | 0 | Oldbury United |
| 14/08/1999 | Willenhall Town | 1 | 0 | Bloxwich Town (R) |