| West Midlands Premier | ||||
| Date | Home | H | A | Away |
| 13/05/2000 | Bustleholme | 1 | 2 | Little Drayton Rangers (P) |
| 13/05/2000 | Kington Town (-6) | 3 | 3 | Darlaston Town |
| 13/05/2000 | Malvern Town | 1 | 4 | Ettingshall Holy Trinity |
| 13/05/2000 | Wolverhampton Casuals | 2 | 0 | Stafford Town |
| 10/05/2000 | Brierley Hill Town | 0 | 0 | Causeway United (P) |
| 10/05/2000 | Bustleholme | 0 | 3 | Tipton Town |
| 10/05/2000 | Stafford Town | 2 | 0 | Heath Hayes (P) |
| 09/05/2000 | Stafford Town | 4 | 1 | Ettingshall Holy Trinity |
| 09/05/2000 | Wolverhampton Casuals | 6 | 0 | Kington Town (-6) |
| 08/05/2000 | Gornal Athletic | 0 | 3 | Causeway United (P) |
| 08/05/2000 | Smethwick Rangers | 2 | 0 | Brierley Hill Town |
| 06/05/2000 | Brierley Hill Town | 1 | 3 | Stafford Town |
| 06/05/2000 | Causeway United (P) | 2 | 0 | Bandon |
| 06/05/2000 | Dudley Town | 2 | 0 | Tipton Town |
| 06/05/2000 | Ettingshall Holy Trinity | 1 | 2 | Kington Town (-6) |
| 06/05/2000 | Ludlow Town | 1 | 1 | Walsall Wood |
| 06/05/2000 | Malvern Town | 1 | 1 | Smethwick Rangers |
| 04/05/2000 | Bandon | 1 | 1 | Smethwick Rangers |
| 03/05/2000 | Bustleholme | 3 | 4 | Gornal Athletic |
| 03/05/2000 | Causeway United (P) | 2 | 0 | Malvern Town |
| 02/05/2000 | Dudley Town | 1 | 1 | Lye Town |
| 01/05/2000 | Brierley Hill Town | 1 | 1 | Smethwick Rangers |
| 01/05/2000 | Causeway United (P) | 1 | 0 | Westfields |
| 01/05/2000 | Heath Hayes (P) | 4 | 1 | Ettingshall Holy Trinity |
| 01/05/2000 | Kington Town (-6) | 0 | 1 | Tividale |
| 01/05/2000 | Little Drayton Rangers (P) | 3 | 3 | Walsall Wood |
| 01/05/2000 | Ludlow Town | 1 | 2 | Wolverhampton Casuals |
| 01/05/2000 | Stafford Town | 1 | 0 | Malvern Town |
| 29/04/2000 | Brierley Hill Town | 0 | 3 | Tividale |
| 29/04/2000 | Ettingshall Holy Trinity | 0 | 0 | Bustleholme |
| 29/04/2000 | Kington Town (-6) | 0 | 1 | Causeway United (P) |
| 29/04/2000 | Little Drayton Rangers (P) | 0 | 1 | Heath Hayes (P) |
| 29/04/2000 | Lye Town | 3 | 3 | Bandon |
| 29/04/2000 | Smethwick Rangers | 2 | 7 | Darlaston Town |
| 29/04/2000 | Stafford Town | 4 | 0 | Star |
| 29/04/2000 | Tipton Town | 1 | 1 | Ludlow Town |
| 29/04/2000 | Westfields | 1 | 1 | Dudley Town |
| 29/04/2000 | Wolverhampton Casuals | 1 | 0 | Malvern Town |
| 27/04/2000 | Bandon | 1 | 1 | Star |
| 27/04/2000 | Walsall Wood | 1 | 4 | Causeway United (P) |
| 26/04/2000 | Stafford Town | 4 | 1 | Smethwick Rangers |
| 24/04/2000 | Causeway United (P) | 4 | 2 | Brierley Hill Town |
| 24/04/2000 | Gornal Athletic | 0 | 2 | Ettingshall Holy Trinity |
| 24/04/2000 | Ludlow Town | 1 | 1 | Little Drayton Rangers (P) |
| 24/04/2000 | Malvern Town | 4 | 2 | Lye Town |
| 24/04/2000 | Walsall Wood | 1 | 4 | Darlaston Town |
| 24/04/2000 | Westfields | 0 | 1 | Kington Town (-6) |
| 22/04/2000 | Little Drayton Rangers (P) | 1 | 2 | Dudley Town |
| 22/04/2000 | Star | 2 | 2 | Wolverhampton Casuals |
| 22/04/2000 | Tividale | 2 | 2 | Westfields |
| 20/04/2000 | Dudley Town | 1 | 1 | Star |
| 19/04/2000 | Heath Hayes (P) | 0 | 2 | Darlaston Town |
| 19/04/2000 | Smethwick Rangers | 3 | 5 | Bustleholme |
| 15/04/2000 | Darlaston Town | 4 | 0 | Ettingshall Holy Trinity |
| 15/04/2000 | Gornal Athletic | 0 | 1 | Bandon |
| 15/04/2000 | Kington Town (-6) | 1 | 1 | Brierley Hill Town |
| 15/04/2000 | Little Drayton Rangers (P) | 1 | 1 | Stafford Town |
| 15/04/2000 | Ludlow Town | 4 | 2 | Dudley Town |
| 15/04/2000 | Star | 2 | 5 | Westfields |
| 15/04/2000 | Tipton Town | 2 | 8 | Malvern Town |
| 15/04/2000 | Wolverhampton Casuals | 5 | 2 | Tividale |
| 11/04/2000 | Bandon | 3 | 1 | Tipton Town |
| 08/04/2000 | Dudley Town | 0 | 2 | Wolverhampton Casuals |
| 08/04/2000 | Ettingshall Holy Trinity | 1 | 2 | Westfields |
| 08/04/2000 | Malvern Town | 2 | 2 | Ludlow Town |
| 08/04/2000 | Smethwick Rangers | 0 | 2 | Heath Hayes (P) |
| 08/04/2000 | Stafford Town | 3 | 0 | Lye Town |
| 08/04/2000 | Tipton Town | 4 | 4 | Bustleholme |
| 08/04/2000 | Tividale | 0 | 1 | Star |
| 08/04/2000 | Walsall Wood | 2 | 1 | Gornal Athletic |
| 05/04/2000 | Bustleholme | 1 | 2 | Ludlow Town |
| 04/04/2000 | Bandon | 2 | 1 | Wolverhampton Casuals |
| 01/04/2000 | Bandon | 2 | 1 | Brierley Hill Town |
| 01/04/2000 | Causeway United (P) | 2 | 1 | Kington Town (-6) |
| 01/04/2000 | Darlaston Town | 4 | 1 | Westfields |
| 01/04/2000 | Ettingshall Holy Trinity | 4 | 0 | Heath Hayes (P) |
| 01/04/2000 | Gornal Athletic | 1 | 1 | Bustleholme |
| 01/04/2000 | Lye Town | 0 | 0 | Star |
| 01/04/2000 | Malvern Town | 2 | 1 | Little Drayton Rangers (P) |
| 01/04/2000 | Tipton Town | 0 | 2 | Stafford Town |
| 01/04/2000 | Walsall Wood | 1 | 1 | Tividale |
| 01/04/2000 | Wolverhampton Casuals | 3 | 2 | Ludlow Town |
| 29/03/2000 | Lye Town | 2 | 3 | Ettingshall Holy Trinity |
| 29/03/2000 | Tipton Town | 2 | 1 | Brierley Hill Town |
| 28/03/2000 | Heath Hayes (P) | 2 | 1 | Malvern Town |
| 28/03/2000 | Ludlow Town | 3 | 1 | Smethwick Rangers |
| 28/03/2000 | Tividale | 1 | 2 | Stafford Town |
| 28/03/2000 | Westfields | 2 | 0 | Causeway United (P) |
| 25/03/2000 | Brierley Hill Town | 0 | 1 | Westfields |
| 25/03/2000 | Darlaston Town | 3 | 1 | Bandon |
| 25/03/2000 | Ettingshall Holy Trinity | 1 | 4 | Causeway United (P) |
| 25/03/2000 | Gornal Athletic | 0 | 1 | Walsall Wood |
| 25/03/2000 | Kington Town (-6) | 2 | 1 | Heath Hayes (P) |
| 25/03/2000 | Little Drayton Rangers (P) | 3 | 0 | Star |
| 25/03/2000 | Ludlow Town | 0 | 0 | Lye Town |
| 25/03/2000 | Smethwick Rangers | 2 | 1 | Malvern Town |
| 25/03/2000 | Tipton Town | 3 | 0 | Wolverhampton Casuals |
| 25/03/2000 | Tividale | 1 | 2 | Dudley Town |
| 22/03/2000 | Lye Town | 0 | 2 | Wolverhampton Casuals |
| 22/03/2000 | Stafford Town | 3 | 0 | Kington Town (-6) |
| 21/03/2000 | Bandon | 2 | 0 | Tividale |
| 21/03/2000 | Darlaston Town | 4 | 1 | Walsall Wood |
| 21/03/2000 | Gornal Athletic | 0 | 2 | Dudley Town |
| 21/03/2000 | Westfields | 2 | 1 | Star |
| 18/03/2000 | Bandon | 2 | 0 | Ettingshall Holy Trinity |
| 18/03/2000 | Brierley Hill Town | 2 | 4 | Darlaston Town |
| 18/03/2000 | Bustleholme | 3 | 3 | Heath Hayes (P) |
| 18/03/2000 | Dudley Town | 3 | 1 | Smethwick Rangers |
| 18/03/2000 | Malvern Town | 0 | 1 | Gornal Athletic |
| 18/03/2000 | Star | 0 | 2 | Ludlow Town |
| 18/03/2000 | Walsall Wood | 2 | 0 | Kington Town (-6) |
| 18/03/2000 | Westfields | 0 | 2 | Stafford Town |
| 18/03/2000 | Wolverhampton Casuals | 1 | 1 | Little Drayton Rangers (P) |
| 15/03/2000 | Little Drayton Rangers (P) | 2 | 1 | Bustleholme |
| 15/03/2000 | Stafford Town | 1 | 0 | Wolverhampton Casuals |
| 14/03/2000 | Darlaston Town | 2 | 1 | Heath Hayes (P) |
| 14/03/2000 | Gornal Athletic | 2 | 2 | Kington Town (-6) |
| 11/03/2000 | Ettingshall Holy Trinity | 1 | 1 | Dudley Town |
| 11/03/2000 | Gornal Athletic | 0 | 1 | Tividale |
| 11/03/2000 | Kington Town (-6) | 3 | 1 | Wolverhampton Casuals |
| 11/03/2000 | Little Drayton Rangers (P) | 1 | 0 | Bandon |
| 11/03/2000 | Ludlow Town | 0 | 2 | Causeway United (P) |
| 11/03/2000 | Smethwick Rangers | 3 | 2 | Star |
| 11/03/2000 | Stafford Town | 1 | 1 | Darlaston Town |
| 11/03/2000 | Tipton Town | 1 | 1 | Lye Town |
| 08/03/2000 | Heath Hayes (P) | 0 | 1 | Wolverhampton Casuals |
| 08/03/2000 | Little Drayton Rangers (P) | 3 | 3 | Tividale |
| 04/03/2000 | Bandon | 3 | 1 | Malvern Town |
| 04/03/2000 | Bustleholme | 0 | 1 | Darlaston Town |
| 04/03/2000 | Dudley Town | 0 | 1 | Kington Town (-6) |
| 04/03/2000 | Heath Hayes (P) | 0 | 2 | Lye Town |
| 04/03/2000 | Ludlow Town | 0 | 0 | Tipton Town |
| 04/03/2000 | Smethwick Rangers | 2 | 3 | Causeway United (P) |
| 04/03/2000 | Star | 0 | 3 | Little Drayton Rangers (P) |
| 04/03/2000 | Walsall Wood | 1 | 3 | Ettingshall Holy Trinity |
| 04/03/2000 | Westfields | 1 | 1 | Brierley Hill Town |
| 04/03/2000 | Wolverhampton Casuals | 2 | 1 | Gornal Athletic |
| 26/02/2000 | Brierley Hill Town | 0 | 2 | Heath Hayes (P) |
| 26/02/2000 | Causeway United (P) | 1 | 0 | Ludlow Town |
| 26/02/2000 | Darlaston Town | 3 | 2 | Dudley Town |
| 26/02/2000 | Ettingshall Holy Trinity | 2 | 1 | Wolverhampton Casuals |
| 26/02/2000 | Gornal Athletic | 0 | 3 | Stafford Town |
| 26/02/2000 | Kington Town (-6) | 0 | 1 | Little Drayton Rangers (P) |
| 26/02/2000 | Lye Town | 0 | 1 | Bustleholme |
| 26/02/2000 | Smethwick Rangers | 0 | 3 | Bandon |
| 26/02/2000 | Star | 2 | 0 | Walsall Wood |
| 26/02/2000 | Tipton Town | 2 | 2 | Westfields |
| 26/02/2000 | Tividale | 2 | 2 | Malvern Town |
| 23/02/2000 | Little Drayton Rangers (P) | 1 | 0 | Ettingshall Holy Trinity |
| 23/02/2000 | Smethwick Rangers | 1 | 2 | Lye Town |
| 22/02/2000 | Dudley Town | 0 | 0 | Ludlow Town |
| 19/02/2000 | Bandon | 1 | 0 | Westfields |
| 19/02/2000 | Brierley Hill Town | 1 | 3 | Wolverhampton Casuals |
| 19/02/2000 | Bustleholme | 1 | 4 | Causeway United (P) |
| 19/02/2000 | Dudley Town | 4 | 0 | Ettingshall Holy Trinity |
| 19/02/2000 | Heath Hayes (P) | 3 | 1 | Ludlow Town |
| 19/02/2000 | Little Drayton Rangers (P) | 2 | 1 | Lye Town |
| 19/02/2000 | Malvern Town | 2 | 3 | Darlaston Town |
| 19/02/2000 | Star | 1 | 0 | Gornal Athletic |
| 19/02/2000 | Tividale | 0 | 1 | Kington Town (-6) |
| 19/02/2000 | Walsall Wood | 3 | 0 | Tipton Town |
| 16/02/2000 | Ettingshall Holy Trinity | 0 | 0 | Star |
| 16/02/2000 | Smethwick Rangers | 1 | 5 | Dudley Town |
| 15/02/2000 | Ludlow Town | 0 | 3 | Malvern Town |
| 15/02/2000 | Westfields | 0 | 1 | Tividale |
| 12/02/2000 | Darlaston Town | 2 | 3 | Tividale |
| 12/02/2000 | Gornal Athletic | 2 | 1 | Ludlow Town |
| 12/02/2000 | Kington Town (-6) | 1 | 5 | Lye Town |
| 12/02/2000 | Malvern Town | 5 | 0 | Heath Hayes (P) |
| 12/02/2000 | Smethwick Rangers | 2 | 1 | Tipton Town |
| 12/02/2000 | Stafford Town | 4 | 1 | Dudley Town |
| 12/02/2000 | Walsall Wood | 1 | 1 | Bandon |
| 12/02/2000 | Westfields | 0 | 0 | Wolverhampton Casuals |
| 09/02/2000 | Walsall Wood | 2 | 1 | Brierley Hill Town |
| 08/02/2000 | Ludlow Town | 1 | 2 | Tividale |
| 08/02/2000 | Wolverhampton Casuals | 6 | 1 | Ettingshall Holy Trinity |
| 05/02/2000 | Bandon | 6 | 0 | Kington Town (-6) |
| 05/02/2000 | Dudley Town | 1 | 4 | Causeway United (P) |
| 05/02/2000 | Ludlow Town | 0 | 4 | Stafford Town |
| 05/02/2000 | Lye Town | 0 | 3 | Gornal Athletic |
| 05/02/2000 | Malvern Town | 0 | 0 | Brierley Hill Town |
| 05/02/2000 | Star | 0 | 2 | Heath Hayes (P) |
| 05/02/2000 | Tipton Town | 2 | 1 | Little Drayton Rangers (P) |
| 05/02/2000 | Tividale | 1 | 0 | Ettingshall Holy Trinity |
| 05/02/2000 | Walsall Wood | 5 | 2 | Smethwick Rangers |
| 05/02/2000 | Westfields | 4 | 1 | Bustleholme |
| 05/02/2000 | Wolverhampton Casuals | 4 | 0 | Darlaston Town |
| 29/01/2000 | Bustleholme | 2 | 0 | Dudley Town |
| 29/01/2000 | Causeway United (P) | 1 | 0 | Ettingshall Holy Trinity |
| 29/01/2000 | Darlaston Town | 0 | 1 | Stafford Town |
| 29/01/2000 | Gornal Athletic | 5 | 2 | Little Drayton Rangers (P) |
| 29/01/2000 | Kington Town (-6) | 3 | 0 | Tipton Town |
| 29/01/2000 | Lye Town | 3 | 1 | Ludlow Town |
| 29/01/2000 | Smethwick Rangers | 2 | 2 | Westfields |
| 29/01/2000 | Walsall Wood | 0 | 1 | Malvern Town |
| 29/01/2000 | Wolverhampton Casuals | 3 | 0 | Heath Hayes (P) |
| 22/01/2000 | Causeway United (P) | 1 | 0 | Walsall Wood |
| 22/01/2000 | Dudley Town | 1 | 4 | Bandon |
| 22/01/2000 | Ettingshall Holy Trinity | 1 | 3 | Lye Town |
| 22/01/2000 | Heath Hayes (P) | 0 | 2 | Tividale |
| 22/01/2000 | Little Drayton Rangers (P) | 2 | 1 | Smethwick Rangers |
| 22/01/2000 | Ludlow Town | 1 | 2 | Kington Town (-6) |
| 22/01/2000 | Malvern Town | 3 | 1 | Bustleholme |
| 22/01/2000 | Stafford Town | 3 | 2 | Westfields |
| 22/01/2000 | Star | 1 | 3 | Darlaston Town |
| 22/01/2000 | Tipton Town | 1 | 4 | Gornal Athletic |
| 22/01/2000 | Wolverhampton Casuals | 0 | 0 | Brierley Hill Town |
| 15/01/2000 | Brierley Hill Town | 2 | 1 | Little Drayton Rangers (P) |
| 15/01/2000 | Bustleholme | 2 | 0 | Tividale |
| 15/01/2000 | Causeway United (P) | 3 | 0 | Star |
| 15/01/2000 | Darlaston Town | 3 | 2 | Ludlow Town |
| 15/01/2000 | Ettingshall Holy Trinity | 2 | 2 | Tipton Town |
| 15/01/2000 | Gornal Athletic | 4 | 1 | Westfields |
| 15/01/2000 | Kington Town (-6) | 4 | 2 | Smethwick Rangers |
| 15/01/2000 | Malvern Town | 0 | 0 | Dudley Town |
| 15/01/2000 | Walsall Wood | 2 | 3 | Lye Town |
| 12/01/2000 | Lye Town | 3 | 0 | Walsall Wood |
| 12/01/2000 | Smethwick Rangers | 2 | 3 | Wolverhampton Casuals |
| 12/01/2000 | Tipton Town | 1 | 2 | Darlaston Town |
| 08/01/2000 | Brierley Hill Town | 1 | 3 | Star |
| 08/01/2000 | Dudley Town | 2 | 0 | Walsall Wood |
| 08/01/2000 | Ludlow Town | 3 | 1 | Ettingshall Holy Trinity |
| 08/01/2000 | Lye Town | 0 | 2 | Kington Town (-6) |
| 08/01/2000 | Malvern Town | 4 | 2 | Westfields |
| 08/01/2000 | Smethwick Rangers | 0 | 1 | Gornal Athletic |
| 08/01/2000 | Stafford Town | 2 | 1 | Tividale |
| 08/01/2000 | Tipton Town | 0 | 1 | Heath Hayes (P) |
| 08/01/2000 | Wolverhampton Casuals | 8 | 1 | Bustleholme |
| 03/01/2000 | Bandon | 2 | 1 | Stafford Town |
| 03/01/2000 | Brierley Hill Town | 1 | 0 | Dudley Town |
| 03/01/2000 | Kington Town (-6) | 0 | 3 | Malvern Town |
| 03/01/2000 | Little Drayton Rangers (P) | 1 | 1 | Westfields |
| 03/01/2000 | Lye Town | 0 | 2 | Causeway United (P) |
| 03/01/2000 | Tividale | 1 | 1 | Darlaston Town |
| 27/12/1999 | Darlaston Town | 7 | 2 | Bustleholme |
| 27/12/1999 | Dudley Town | 2 | 2 | Gornal Athletic |
| 27/12/1999 | Kington Town (-6) | 1 | 0 | Westfields |
| 27/12/1999 | Little Drayton Rangers (P) | 1 | 5 | Ludlow Town |
| 27/12/1999 | Lye Town | 2 | 3 | Brierley Hill Town |
| 27/12/1999 | Malvern Town | 1 | 2 | Stafford Town |
| 27/12/1999 | Star | 1 | 4 | Bandon |
| 27/12/1999 | Tividale | 1 | 2 | Causeway United (P) |
| 18/12/1999 | Bandon | 3 | 1 | Lye Town |
| 18/12/1999 | Brierley Hill Town | 3 | 0 | Ludlow Town |
| 18/12/1999 | Bustleholme | 2 | 3 | Stafford Town |
| 18/12/1999 | Darlaston Town | 2 | 0 | Gornal Athletic |
| 18/12/1999 | Ettingshall Holy Trinity | 3 | 1 | Smethwick Rangers |
| 18/12/1999 | Heath Hayes (P) | 2 | 0 | Little Drayton Rangers (P) |
| 18/12/1999 | Malvern Town | 1 | 1 | Tividale |
| 18/12/1999 | Walsall Wood | 0 | 0 | Star |
| 18/12/1999 | Westfields | 4 | 1 | Tipton Town |
| 11/12/1999 | Star | 0 | 0 | Bustleholme |
| 11/12/1999 | Westfields | 1 | 2 | Bandon |
| 04/12/1999 | Bandon | 0 | 0 | Ludlow Town |
| 04/12/1999 | Brierley Hill Town | 0 | 2 | Tipton Town |
| 04/12/1999 | Bustleholme | 2 | 4 | Lye Town |
| 04/12/1999 | Causeway United (P) | 3 | 1 | Little Drayton Rangers (P) |
| 04/12/1999 | Darlaston Town | 4 | 2 | Smethwick Rangers |
| 04/12/1999 | Dudley Town | 0 | 1 | Tividale |
| 04/12/1999 | Ettingshall Holy Trinity | 1 | 1 | Gornal Athletic |
| 04/12/1999 | Heath Hayes (P) | 2 | 3 | Kington Town (-6) |
| 04/12/1999 | Star | 1 | 0 | Malvern Town |
| 04/12/1999 | Walsall Wood | 2 | 2 | Stafford Town |
| 04/12/1999 | Wolverhampton Casuals | 3 | 0 | Westfields |
| 01/12/1999 | Little Drayton Rangers (P) | 3 | 1 | Wolverhampton Casuals |
| 01/12/1999 | Tipton Town | 2 | 1 | Star |
| 30/11/1999 | Bandon | 3 | 0 | Heath Hayes (P) |
| 27/11/1999 | Gornal Athletic | 1 | 0 | Darlaston Town |
| 27/11/1999 | Little Drayton Rangers (P) | 4 | 1 | Brierley Hill Town |
| 27/11/1999 | Ludlow Town | 1 | 2 | Bustleholme |
| 27/11/1999 | Lye Town | 1 | 2 | Heath Hayes (P) |
| 27/11/1999 | Smethwick Rangers | 1 | 1 | Ettingshall Holy Trinity |
| 27/11/1999 | Star | 0 | 0 | Dudley Town |
| 27/11/1999 | Tipton Town | 0 | 1 | Bandon |
| 27/11/1999 | Tividale | 2 | 4 | Wolverhampton Casuals |
| 27/11/1999 | Westfields | 0 | 0 | Walsall Wood |
| 24/11/1999 | Ettingshall Holy Trinity | 3 | 1 | Bandon |
| 24/11/1999 | Little Drayton Rangers (P) | 0 | 2 | Tipton Town |
| 24/11/1999 | Walsall Wood | 0 | 6 | Wolverhampton Casuals |
| 23/11/1999 | Dudley Town | 2 | 0 | Heath Hayes (P) |
| 23/11/1999 | Kington Town (-6) | 5 | 2 | Star |
| 20/11/1999 | Bandon | 0 | 1 | Causeway United (P) |
| 20/11/1999 | Darlaston Town | 0 | 1 | Kington Town (-6) |
| 20/11/1999 | Dudley Town | 0 | 1 | Stafford Town |
| 20/11/1999 | Ettingshall Holy Trinity | 2 | 1 | Malvern Town |
| 20/11/1999 | Heath Hayes (P) | 1 | 3 | Gornal Athletic |
| 20/11/1999 | Lye Town | 2 | 2 | Little Drayton Rangers (P) |
| 20/11/1999 | Tividale | 6 | 0 | Tipton Town |
| 20/11/1999 | Walsall Wood | 0 | 1 | Ludlow Town |
| 20/11/1999 | Wolverhampton Casuals | 1 | 2 | Star |
| 16/11/1999 | Lye Town | 0 | 0 | Dudley Town |
| 13/11/1999 | Causeway United (P) | 2 | 3 | Wolverhampton Casuals |
| 13/11/1999 | Gornal Athletic | 1 | 1 | Brierley Hill Town |
| 13/11/1999 | Star | 0 | 1 | Tividale |
| 13/11/1999 | Tipton Town | 4 | 1 | Walsall Wood |
| 13/11/1999 | Westfields | 4 | 0 | Ettingshall Holy Trinity |
| 10/11/1999 | Lye Town | 4 | 1 | Westfields |
| 09/11/1999 | Bandon | 4 | 2 | Gornal Athletic |
| 06/11/1999 | Brierley Hill Town | 2 | 1 | Kington Town (-6) |
| 06/11/1999 | Ettingshall Holy Trinity | 1 | 4 | Darlaston Town |
| 06/11/1999 | Heath Hayes (P) | 0 | 3 | Causeway United (P) |
| 06/11/1999 | Malvern Town | 1 | 2 | Tipton Town |
| 06/11/1999 | Stafford Town | 3 | 0 | Bustleholme |
| 06/11/1999 | Tividale | 1 | 0 | Smethwick Rangers |
| 06/11/1999 | Walsall Wood | 3 | 2 | Little Drayton Rangers (P) |
| 06/11/1999 | Wolverhampton Casuals | 1 | 0 | Lye Town |
| 03/11/1999 | Bustleholme | 1 | 2 | Brierley Hill Town |
| 03/11/1999 | Ludlow Town | 1 | 1 | Star |
| 03/11/1999 | Stafford Town | 5 | 0 | Tipton Town |
| 30/10/1999 | Causeway United (P) | 2 | 0 | Smethwick Rangers |
| 30/10/1999 | Ettingshall Holy Trinity | 3 | 3 | Walsall Wood |
| 30/10/1999 | Heath Hayes (P) | 0 | 1 | Brierley Hill Town |
| 30/10/1999 | Kington Town (-6) | 3 | 2 | Bandon |
| 30/10/1999 | Little Drayton Rangers (P) | 1 | 1 | Malvern Town |
| 30/10/1999 | Lye Town | 0 | 2 | Tividale |
| 30/10/1999 | Star | 1 | 2 | Stafford Town |
| 30/10/1999 | Tipton Town | 3 | 1 | Dudley Town |
| 30/10/1999 | Westfields | 2 | 4 | Darlaston Town |
| 27/10/1999 | Heath Hayes (P) | 0 | 3 | Stafford Town |
| 23/10/1999 | Brierley Hill Town | 1 | 1 | Ettingshall Holy Trinity |
| 23/10/1999 | Bustleholme | 1 | 0 | Kington Town (-6) |
| 23/10/1999 | Darlaston Town | 5 | 2 | Causeway United (P) |
| 23/10/1999 | Heath Hayes (P) | 1 | 1 | Dudley Town |
| 23/10/1999 | Stafford Town | 1 | 1 | Bandon |
| 23/10/1999 | Star | 2 | 3 | Lye Town |
| 23/10/1999 | Tividale | 3 | 1 | Ludlow Town |
| 23/10/1999 | Westfields | 0 | 4 | Little Drayton Rangers (P) |
| 23/10/1999 | Wolverhampton Casuals | 3 | 2 | Tipton Town |
| 20/10/1999 | Walsall Wood | 2 | 4 | Heath Hayes (P) |
| 16/10/1999 | Causeway United (P) | 3 | 2 | Bustleholme |
| 16/10/1999 | Darlaston Town | 3 | 2 | Brierley Hill Town |
| 16/10/1999 | Gornal Athletic | 0 | 1 | Malvern Town |
| 16/10/1999 | Kington Town (-6) | 7 | 1 | Walsall Wood |
| 16/10/1999 | Lye Town | 2 | 0 | Stafford Town |
| 16/10/1999 | Tipton Town | 1 | 3 | Tividale |
| 16/10/1999 | Westfields | 0 | 4 | Heath Hayes (P) |
| 13/10/1999 | Bustleholme | 1 | 0 | Smethwick Rangers |
| 12/10/1999 | Gornal Athletic | 0 | 2 | Star |
| 09/10/1999 | Bandon | 1 | 2 | Darlaston Town |
| 09/10/1999 | Brierley Hill Town | 3 | 1 | Walsall Wood |
| 09/10/1999 | Bustleholme | 1 | 1 | Ettingshall Holy Trinity |
| 09/10/1999 | Causeway United (P) | 5 | 1 | Gornal Athletic |
| 09/10/1999 | Heath Hayes (P) | 4 | 0 | Westfields |
| 09/10/1999 | Kington Town (-6) | 3 | 0 | Dudley Town |
| 09/10/1999 | Lye Town | 1 | 0 | Malvern Town |
| 09/10/1999 | Stafford Town | 5 | 0 | Ludlow Town |
| 09/10/1999 | Star | 0 | 5 | Tipton Town |
| 09/10/1999 | Tividale | 1 | 0 | Little Drayton Rangers (P) |
| 09/10/1999 | Wolverhampton Casuals | 2 | 2 | Smethwick Rangers |
| 06/10/1999 | Bustleholme | 5 | 2 | Walsall Wood |
| 06/10/1999 | Causeway United (P) | 2 | 0 | Tipton Town |
| 06/10/1999 | Smethwick Rangers | 2 | 2 | Tividale |
| 06/10/1999 | Stafford Town | 2 | 1 | Little Drayton Rangers (P) |
| 05/10/1999 | Gornal Athletic | 1 | 4 | Wolverhampton Casuals |
| 02/10/1999 | Brierley Hill Town | 2 | 3 | Bandon |
| 02/10/1999 | Causeway United (P) | 1 | 2 | Darlaston Town |
| 02/10/1999 | Dudley Town | 1 | 1 | Little Drayton Rangers (P) |
| 02/10/1999 | Kington Town (-6) | 3 | 2 | Bustleholme |
| 02/10/1999 | Ludlow Town | 2 | 0 | Westfields |
| 02/10/1999 | Lye Town | 2 | 2 | Tipton Town |
| 02/10/1999 | Star | 1 | 2 | Smethwick Rangers |
| 02/10/1999 | Tividale | 0 | 2 | Gornal Athletic |
| 29/09/1999 | Ettingshall Holy Trinity | 0 | 2 | Brierley Hill Town |
| 28/09/1999 | Bandon | 1 | 1 | Walsall Wood |
| 25/09/1999 | Brierley Hill Town | 3 | 3 | Bustleholme |
| 25/09/1999 | Heath Hayes (P) | 1 | 2 | Bandon |
| 25/09/1999 | Little Drayton Rangers (P) | 1 | 2 | Causeway United (P) |
| 25/09/1999 | Tipton Town | 1 | 1 | Ettingshall Holy Trinity |
| 22/09/1999 | Bustleholme | 1 | 3 | Bandon |
| 22/09/1999 | Heath Hayes (P) | 4 | 1 | Star |
| 22/09/1999 | Smethwick Rangers | 4 | 1 | Walsall Wood |
| 22/09/1999 | Stafford Town | 3 | 0 | Gornal Athletic |
| 21/09/1999 | Malvern Town | 0 | 1 | Causeway United (P) |
| 21/09/1999 | Westfields | 2 | 1 | Lye Town |
| 18/09/1999 | Brierley Hill Town | 2 | 3 | Malvern Town |
| 18/09/1999 | Bustleholme | 4 | 1 | Westfields |
| 18/09/1999 | Causeway United (P) | 0 | 0 | Dudley Town |
| 18/09/1999 | Darlaston Town | 5 | 2 | Wolverhampton Casuals |
| 18/09/1999 | Ettingshall Holy Trinity | 2 | 1 | Tividale |
| 18/09/1999 | Gornal Athletic | 1 | 3 | Lye Town |
| 18/09/1999 | Heath Hayes (P) | 2 | 1 | Walsall Wood |
| 18/09/1999 | Kington Town (-6) | 3 | 4 | Stafford Town |
| 18/09/1999 | Smethwick Rangers | 2 | 1 | Ludlow Town |
| 15/09/1999 | Lye Town | 1 | 2 | Smethwick Rangers |
| 15/09/1999 | Star | 1 | 4 | Kington Town (-6) |
| 14/09/1999 | Darlaston Town | 3 | 1 | Malvern Town |
| 14/09/1999 | Westfields | 2 | 3 | Gornal Athletic |
| 11/09/1999 | Dudley Town | 0 | 2 | Brierley Hill Town |
| 11/09/1999 | Little Drayton Rangers (P) | 2 | 2 | Darlaston Town |
| 11/09/1999 | Ludlow Town | 0 | 4 | Gornal Athletic |
| 11/09/1999 | Malvern Town | 3 | 1 | Bandon |
| 11/09/1999 | Star | 1 | 2 | Ettingshall Holy Trinity |
| 11/09/1999 | Tipton Town | 1 | 4 | Smethwick Rangers |
| 11/09/1999 | Tividale | 2 | 3 | Heath Hayes (P) |
| 11/09/1999 | Walsall Wood | 1 | 1 | Bustleholme |
| 11/09/1999 | Wolverhampton Casuals | 1 | 2 | Causeway United (P) |
| 08/09/1999 | Bustleholme | 0 | 2 | Malvern Town |
| 08/09/1999 | Causeway United (P) | 3 | 0 | Tividale |
| 08/09/1999 | Stafford Town | 4 | 1 | Walsall Wood |
| 07/09/1999 | Darlaston Town | 2 | 0 | Star |
| 07/09/1999 | Gornal Athletic | 1 | 3 | Tipton Town |
| 07/09/1999 | Kington Town (-6) | 3 | 1 | Ludlow Town |
| 04/09/1999 | Dudley Town | 2 | 1 | Bustleholme |
| 04/09/1999 | Ettingshall Holy Trinity | 1 | 7 | Stafford Town |
| 04/09/1999 | Little Drayton Rangers (P) | 1 | 0 | Gornal Athletic |
| 04/09/1999 | Ludlow Town | 1 | 3 | Heath Hayes (P) |
| 04/09/1999 | Lye Town | 2 | 0 | Darlaston Town |
| 04/09/1999 | Malvern Town | 3 | 1 | Walsall Wood |
| 04/09/1999 | Star | 0 | 2 | Causeway United (P) |
| 04/09/1999 | Tipton Town | 1 | 3 | Kington Town (-6) |
| 04/09/1999 | Tividale | 3 | 2 | Brierley Hill Town |
| 04/09/1999 | Westfields | 2 | 4 | Smethwick Rangers |
| 04/09/1999 | Wolverhampton Casuals | 1 | 2 | Bandon |
| 30/08/1999 | Bandon | 4 | 0 | Little Drayton Rangers (P) |
| 30/08/1999 | Brierley Hill Town | 2 | 1 | Gornal Athletic |
| 30/08/1999 | Causeway United (P) | 1 | 0 | Lye Town |
| 30/08/1999 | Dudley Town | 0 | 1 | Darlaston Town |
| 30/08/1999 | Malvern Town | 1 | 2 | Kington Town (-6) |
| 30/08/1999 | Tividale | 3 | 3 | Bustleholme |
| 30/08/1999 | Westfields | 1 | 1 | Ludlow Town |
| 28/08/1999 | Bustleholme | 1 | 2 | Wolverhampton Casuals |
| 28/08/1999 | Darlaston Town | 6 | 2 | Lye Town |
| 28/08/1999 | Ettingshall Holy Trinity | 1 | 2 | Ludlow Town |
| 28/08/1999 | Gornal Athletic | 1 | 2 | Smethwick Rangers |
| 28/08/1999 | Heath Hayes (P) | 1 | 1 | Tipton Town |
| 28/08/1999 | Little Drayton Rangers (P) | 0 | 4 | Kington Town (-6) |
| 28/08/1999 | Stafford Town | 2 | 1 | Causeway United (P) |
| 28/08/1999 | Star | 2 | 1 | Brierley Hill Town |
| 28/08/1999 | Tividale | 2 | 1 | Bandon |
| 28/08/1999 | Walsall Wood | 2 | 3 | Dudley Town |
| 28/08/1999 | Westfields | 1 | 6 | Malvern Town |
| 25/08/1999 | Causeway United (P) | 2 | 1 | Heath Hayes (P) |
| 25/08/1999 | Ludlow Town | 4 | 4 | Darlaston Town |
| 25/08/1999 | Smethwick Rangers | 1 | 2 | Little Drayton Rangers (P) |
| 25/08/1999 | Stafford Town | 3 | 0 | Brierley Hill Town |
| 24/08/1999 | Bandon | 2 | 0 | Dudley Town |
| 24/08/1999 | Wolverhampton Casuals | 4 | 2 | Walsall Wood |
| 21/08/1999 | Brierley Hill Town | 0 | 2 | Lye Town |
| 21/08/1999 | Bustleholme | 3 | 1 | Star |
| 21/08/1999 | Causeway United (P) | 1 | 4 | Stafford Town |
| 21/08/1999 | Darlaston Town | 2 | 1 | Tipton Town |
| 21/08/1999 | Dudley Town | 4 | 3 | Westfields |
| 21/08/1999 | Ettingshall Holy Trinity | 0 | 1 | Little Drayton Rangers (P) |
| 21/08/1999 | Heath Hayes (P) | 1 | 1 | Smethwick Rangers |
| 21/08/1999 | Kington Town (-6) | 3 | 2 | Gornal Athletic |
| 21/08/1999 | Ludlow Town | 1 | 2 | Bandon |
| 21/08/1999 | Malvern Town | 1 | 0 | Wolverhampton Casuals |
| 21/08/1999 | Tividale | 2 | 1 | Walsall Wood |
| 18/08/1999 | Heath Hayes (P) | 2 | 1 | Bustleholme |
| 18/08/1999 | Smethwick Rangers | 3 | 1 | Kington Town (-6) |
| 17/08/1999 | Dudley Town | 2 | 1 | Malvern Town |
| 14/08/1999 | Bandon | 2 | 1 | Bustleholme |
| 14/08/1999 | Darlaston Town | 1 | 4 | Little Drayton Rangers (P) |
| 14/08/1999 | Gornal Athletic | 1 | 4 | Heath Hayes (P) |
| 14/08/1999 | Kington Town (-6) | 9 | 1 | Ettingshall Holy Trinity |
| 14/08/1999 | Ludlow Town | 1 | 0 | Brierley Hill Town |
| 14/08/1999 | Malvern Town | 2 | 0 | Star |
| 14/08/1999 | Smethwick Rangers | 0 | 6 | Stafford Town |
| 14/08/1999 | Tipton Town | 0 | 3 | Causeway United (P) |
| 14/08/1999 | Tividale | 1 | 1 | Lye Town |
| 14/08/1999 | Walsall Wood | 2 | 1 | Westfields |
| 14/08/1999 | Wolverhampton Casuals | 2 | 2 | Dudley Town |