| Hellenic Division One | ||||
| Date | Home | H | A | Away |
| 10/05/2000 | Bishops Cleeve | 1 | 0 | Ross Town |
| 10/05/2000 | Cirencester United | 2 | 3 | Wootton Bassett Town |
| 09/05/2000 | Ross Town | 2 | 3 | Old Woodstock Town (P) |
| 08/05/2000 | Ross Town | 0 | 0 | Letcombe |
| 03/05/2000 | Wootton Bassett Town | 2 | 1 | Middle Barton (P) |
| 02/05/2000 | Ross Town | 1 | 2 | Purton |
| 01/05/2000 | Bishops Cleeve | 1 | 4 | Worcester College OB |
| 01/05/2000 | Wootton Bassett Town | 0 | 0 | Letcombe |
| 29/04/2000 | Letcombe | 2 | 2 | Ardley United |
| 29/04/2000 | Purton | 0 | 1 | Middle Barton (P) |
| 29/04/2000 | Worcester College OB | 2 | 2 | Easington Sports |
| 27/04/2000 | Kidlington | 2 | 1 | Headington Amateurs |
| 25/04/2000 | Ardley United | 1 | 1 | Old Woodstock Town (P) |
| 24/04/2000 | Bishops Cleeve | 3 | 0 | Wootton Bassett Town |
| 24/04/2000 | Cirencester United | 1 | 1 | Kidlington |
| 24/04/2000 | Headington Amateurs | 1 | 2 | Easington Sports |
| 22/04/2000 | Clanfield | 0 | 7 | Wootton Bassett Town |
| 22/04/2000 | Headington Amateurs | 0 | 4 | Ardley United |
| 22/04/2000 | Letcombe | 1 | 2 | Kidlington |
| 22/04/2000 | Middle Barton (P) | 1 | 5 | Ross Town |
| 22/04/2000 | Old Woodstock Town (P) | 1 | 2 | Purton |
| 19/04/2000 | Cirencester United | 4 | 0 | Bishops Cleeve |
| 19/04/2000 | Purton | 2 | 0 | Letcombe |
| 08/04/2000 | Bishops Cleeve | 1 | 0 | Middle Barton (P) |
| 08/04/2000 | Cheltenham Saracens | 2 | 0 | Ardley United |
| 08/04/2000 | Cirencester United | 1 | 4 | Ross Town |
| 08/04/2000 | Kidlington | 0 | 4 | Purton |
| 08/04/2000 | Old Woodstock Town (P) | 1 | 0 | Clanfield |
| 08/04/2000 | Worcester College OB | 0 | 3 | Wootton Bassett Town |
| 01/04/2000 | Cirencester United | 1 | 2 | Old Woodstock Town (P) |
| 01/04/2000 | Easington Sports | 2 | 3 | Headington Amateurs |
| 01/04/2000 | Middle Barton (P) | 4 | 2 | Kidlington |
| 01/04/2000 | Purton | 0 | 1 | Cheltenham Saracens |
| 01/04/2000 | Ross Town | 1 | 2 | Ardley United |
| 01/04/2000 | Wootton Bassett Town | 1 | 1 | Bishops Cleeve |
| 28/03/2000 | Ross Town | 0 | 2 | Cheltenham Saracens |
| 25/03/2000 | Cheltenham Saracens | 3 | 0 | Old Woodstock Town (P) |
| 25/03/2000 | Cirencester United | 2 | 1 | Headington Amateurs |
| 25/03/2000 | Clanfield | 2 | 3 | Easington Sports |
| 25/03/2000 | Letcombe | 1 | 1 | Bishops Cleeve |
| 25/03/2000 | Wootton Bassett Town | 2 | 1 | Purton |
| 18/03/2000 | Bishops Cleeve | 2 | 1 | Letcombe |
| 18/03/2000 | Clanfield | 1 | 1 | Headington Amateurs |
| 18/03/2000 | Easington Sports | 1 | 4 | Cheltenham Saracens |
| 18/03/2000 | Kidlington | 1 | 1 | Old Woodstock Town (P) |
| 11/03/2000 | Ardley United | 0 | 0 | Wootton Bassett Town |
| 11/03/2000 | Cheltenham Saracens | 2 | 1 | Worcester College OB |
| 11/03/2000 | Clanfield | 1 | 2 | Bishops Cleeve |
| 11/03/2000 | Letcombe | 3 | 3 | Easington Sports |
| 11/03/2000 | Old Woodstock Town (P) | 1 | 0 | Cirencester United |
| 04/03/2000 | Ardley United | 1 | 2 | Clanfield |
| 04/03/2000 | Cheltenham Saracens | 1 | 1 | Middle Barton (P) |
| 04/03/2000 | Cirencester United | 0 | 1 | Worcester College OB |
| 04/03/2000 | Easington Sports | 1 | 0 | Old Woodstock Town (P) |
| 04/03/2000 | Headington Amateurs | 2 | 0 | Ross Town |
| 26/02/2000 | Ardley United | 2 | 0 | Middle Barton (P) |
| 26/02/2000 | Cheltenham Saracens | 3 | 1 | Easington Sports |
| 26/02/2000 | Old Woodstock Town (P) | 4 | 1 | Headington Amateurs |
| 26/02/2000 | Purton | 2 | 2 | Bishops Cleeve |
| 26/02/2000 | Ross Town | 1 | 0 | Clanfield |
| 26/02/2000 | Wootton Bassett Town | 1 | 2 | Kidlington |
| 26/02/2000 | Worcester College OB | 2 | 1 | Letcombe |
| 19/02/2000 | Bishops Cleeve | 2 | 2 | Old Woodstock Town (P) |
| 19/02/2000 | Clanfield | 1 | 1 | Ross Town |
| 19/02/2000 | Easington Sports | 6 | 2 | Cirencester United |
| 19/02/2000 | Kidlington | 0 | 3 | Cheltenham Saracens |
| 19/02/2000 | Letcombe | 0 | 1 | Worcester College OB |
| 19/02/2000 | Middle Barton (P) | 2 | 3 | Purton |
| 19/02/2000 | Wootton Bassett Town | 1 | 1 | Ardley United |
| 12/02/2000 | Bishops Cleeve | 3 | 0 | Kidlington |
| 12/02/2000 | Cheltenham Saracens | 0 | 1 | Wootton Bassett Town |
| 12/02/2000 | Headington Amateurs | 2 | 2 | Middle Barton (P) |
| 12/02/2000 | Purton | 1 | 0 | Ross Town |
| 12/02/2000 | Worcester College OB | 1 | 0 | Clanfield |
| 05/02/2000 | Cirencester United | 0 | 2 | Purton |
| 05/02/2000 | Clanfield | 0 | 4 | Cheltenham Saracens |
| 05/02/2000 | Easington Sports | 4 | 3 | Bishops Cleeve |
| 05/02/2000 | Middle Barton (P) | 1 | 2 | Letcombe |
| 05/02/2000 | Ross Town | 1 | 1 | Kidlington |
| 05/02/2000 | Wootton Bassett Town | 1 | 0 | Headington Amateurs |
| 05/02/2000 | Worcester College OB | 3 | 3 | Old Woodstock Town (P) |
| 29/01/2000 | Ardley United | 4 | 1 | Cirencester United |
| 29/01/2000 | Bishops Cleeve | 2 | 1 | Cheltenham Saracens |
| 29/01/2000 | Headington Amateurs | 0 | 3 | Letcombe |
| 29/01/2000 | Kidlington | 1 | 2 | Wootton Bassett Town |
| 29/01/2000 | Middle Barton (P) | 2 | 0 | Old Woodstock Town (P) |
| 29/01/2000 | Purton | 2 | 2 | Easington Sports |
| 29/01/2000 | Ross Town | 1 | 1 | Worcester College OB |
| 25/01/2000 | Ross Town | 0 | 1 | Bishops Cleeve |
| 22/01/2000 | Ardley United | 1 | 1 | Easington Sports |
| 22/01/2000 | Bishops Cleeve | 2 | 0 | Headington Amateurs |
| 22/01/2000 | Kidlington | 1 | 1 | Clanfield |
| 22/01/2000 | Letcombe | 3 | 0 | Old Woodstock Town (P) |
| 22/01/2000 | Middle Barton (P) | 3 | 1 | Cirencester United |
| 22/01/2000 | Worcester College OB | 1 | 2 | Cheltenham Saracens |
| 15/01/2000 | Cheltenham Saracens | 4 | 1 | Letcombe |
| 15/01/2000 | Cirencester United | 3 | 0 | Clanfield |
| 15/01/2000 | Headington Amateurs | 1 | 0 | Purton |
| 15/01/2000 | Kidlington | 3 | 1 | Middle Barton (P) |
| 15/01/2000 | Wootton Bassett Town | 0 | 0 | Ross Town |
| 08/01/2000 | Cheltenham Saracens | 1 | 0 | Ross Town |
| 08/01/2000 | Easington Sports | 1 | 1 | Kidlington |
| 08/01/2000 | Letcombe | 1 | 2 | Cirencester United |
| 08/01/2000 | Purton | 0 | 0 | Clanfield |
| 08/01/2000 | Worcester College OB | 0 | 2 | Headington Amateurs |
| 03/01/2000 | Headington Amateurs | 1 | 4 | Cheltenham Saracens |
| 03/01/2000 | Kidlington | 1 | 3 | Worcester College OB |
| 03/01/2000 | Old Woodstock Town (P) | 2 | 2 | Middle Barton (P) |
| 03/01/2000 | Purton | 1 | 2 | Ardley United |
| 27/12/1999 | Cheltenham Saracens | 1 | 0 | Cirencester United |
| 27/12/1999 | Headington Amateurs | 3 | 0 | Worcester College OB |
| 27/12/1999 | Kidlington | 1 | 2 | Ardley United |
| 27/12/1999 | Letcombe | 4 | 1 | Clanfield |
| 27/12/1999 | Middle Barton (P) | 2 | 0 | Easington Sports |
| 18/12/1999 | Ardley United | 1 | 2 | Cheltenham Saracens |
| 18/12/1999 | Letcombe | 1 | 0 | Ross Town |
| 18/12/1999 | Wootton Bassett Town | 3 | 1 | Worcester College OB |
| 04/12/1999 | Bishops Cleeve | 1 | 3 | Cirencester United |
| 04/12/1999 | Clanfield | 2 | 0 | Letcombe |
| 04/12/1999 | Easington Sports | 1 | 0 | Wootton Bassett Town |
| 04/12/1999 | Kidlington | 1 | 0 | Ross Town |
| 04/12/1999 | Middle Barton (P) | 3 | 2 | Headington Amateurs |
| 04/12/1999 | Purton | 2 | 5 | Old Woodstock Town (P) |
| 04/12/1999 | Worcester College OB | 1 | 3 | Ardley United |
| 27/11/1999 | Middle Barton (P) | 2 | 1 | Clanfield |
| 27/11/1999 | Old Woodstock Town (P) | 2 | 2 | Ardley United |
| 27/11/1999 | Worcester College OB | 1 | 1 | Bishops Cleeve |
| 20/11/1999 | Bishops Cleeve | 2 | 2 | Easington Sports |
| 20/11/1999 | Cirencester United | 1 | 0 | Ardley United |
| 20/11/1999 | Letcombe | 0 | 1 | Cheltenham Saracens |
| 13/11/1999 | Ardley United | 2 | 0 | Headington Amateurs |
| 13/11/1999 | Cheltenham Saracens | 4 | 1 | Purton |
| 13/11/1999 | Clanfield | 0 | 2 | Kidlington |
| 13/11/1999 | Old Woodstock Town (P) | 1 | 2 | Bishops Cleeve |
| 13/11/1999 | Ross Town | 0 | 3 | Middle Barton (P) |
| 13/11/1999 | Wootton Bassett Town | 3 | 1 | Cirencester United |
| 06/11/1999 | Clanfield | 3 | 2 | Cirencester United |
| 06/11/1999 | Easington Sports | 5 | 1 | Worcester College OB |
| 06/11/1999 | Headington Amateurs | 0 | 3 | Kidlington |
| 06/11/1999 | Middle Barton (P) | 2 | 3 | Ardley United |
| 06/11/1999 | Old Woodstock Town (P) | 2 | 2 | Cheltenham Saracens |
| 06/11/1999 | Purton | 1 | 0 | Wootton Bassett Town |
| 30/10/1999 | Letcombe | 7 | 2 | Purton |
| 23/10/1999 | Ardley United | 3 | 2 | Bishops Cleeve |
| 23/10/1999 | Cheltenham Saracens | 2 | 0 | Clanfield |
| 23/10/1999 | Cirencester United | 1 | 0 | Easington Sports |
| 23/10/1999 | Kidlington | 2 | 1 | Letcombe |
| 23/10/1999 | Ross Town | 4 | 1 | Headington Amateurs |
| 23/10/1999 | Wootton Bassett Town | 4 | 1 | Old Woodstock Town (P) |
| 23/10/1999 | Worcester College OB | 5 | 3 | Purton |
| 16/10/1999 | Clanfield | 2 | 2 | Middle Barton (P) |
| 16/10/1999 | Easington Sports | 1 | 0 | Ardley United |
| 16/10/1999 | Headington Amateurs | 1 | 1 | Wootton Bassett Town |
| 16/10/1999 | Old Woodstock Town (P) | 0 | 1 | Worcester College OB |
| 16/10/1999 | Purton | 3 | 2 | Kidlington |
| 09/10/1999 | Easington Sports | 1 | 2 | Ross Town |
| 02/10/1999 | Ardley United | 3 | 2 | Purton |
| 02/10/1999 | Headington Amateurs | 2 | 2 | Bishops Cleeve |
| 02/10/1999 | Middle Barton (P) | 3 | 2 | Cheltenham Saracens |
| 02/10/1999 | Old Woodstock Town (P) | 2 | 1 | Easington Sports |
| 02/10/1999 | Ross Town | 1 | 0 | Cirencester United |
| 02/10/1999 | Wootton Bassett Town | 4 | 1 | Clanfield |
| 02/10/1999 | Worcester College OB | 4 | 1 | Kidlington |
| 25/09/1999 | Bishops Cleeve | 2 | 3 | Ardley United |
| 25/09/1999 | Clanfield | 2 | 1 | Old Woodstock Town (P) |
| 25/09/1999 | Easington Sports | 5 | 2 | Purton |
| 25/09/1999 | Headington Amateurs | 0 | 3 | Cirencester United |
| 25/09/1999 | Letcombe | 6 | 1 | Wootton Bassett Town |
| 25/09/1999 | Worcester College OB | 1 | 1 | Middle Barton (P) |
| 18/09/1999 | Ardley United | 4 | 3 | Worcester College OB |
| 18/09/1999 | Cheltenham Saracens | 3 | 0 | Headington Amateurs |
| 18/09/1999 | Cirencester United | 1 | 3 | Letcombe |
| 18/09/1999 | Easington Sports | 2 | 1 | Clanfield |
| 18/09/1999 | Middle Barton (P) | 1 | 3 | Wootton Bassett Town |
| 18/09/1999 | Old Woodstock Town (P) | 3 | 1 | Kidlington |
| 11/09/1999 | Clanfield | 6 | 2 | Purton |
| 11/09/1999 | Headington Amateurs | 2 | 1 | Old Woodstock Town (P) |
| 11/09/1999 | Kidlington | 0 | 1 | Bishops Cleeve |
| 11/09/1999 | Letcombe | 0 | 3 | Middle Barton (P) |
| 11/09/1999 | Ross Town | 3 | 1 | Easington Sports |
| 11/09/1999 | Wootton Bassett Town | 1 | 2 | Cheltenham Saracens |
| 11/09/1999 | Worcester College OB | 4 | 1 | Cirencester United |
| 04/09/1999 | Ardley United | 1 | 2 | Ross Town |
| 04/09/1999 | Bishops Cleeve | 1 | 1 | Clanfield |
| 04/09/1999 | Cheltenham Saracens | 1 | 0 | Kidlington |
| 04/09/1999 | Cirencester United | 2 | 1 | Middle Barton (P) |
| 04/09/1999 | Easington Sports | 0 | 4 | Letcombe |
| 04/09/1999 | Old Woodstock Town (P) | 3 | 4 | Wootton Bassett Town |
| 04/09/1999 | Purton | 0 | 2 | Worcester College OB |
| 30/08/1999 | Cheltenham Saracens | 2 | 1 | Bishops Cleeve |
| 30/08/1999 | Clanfield | 1 | 3 | Ardley United |
| 30/08/1999 | Kidlington | 3 | 0 | Easington Sports |
| 30/08/1999 | Letcombe | 5 | 1 | Headington Amateurs |
| 30/08/1999 | Middle Barton (P) | 0 | 2 | Worcester College OB |
| 30/08/1999 | Purton | 1 | 0 | Cirencester United |
| 30/08/1999 | Ross Town | 0 | 0 | Wootton Bassett Town |
| 28/08/1999 | Ardley United | 5 | 1 | Kidlington |
| 28/08/1999 | Bishops Cleeve | 2 | 1 | Purton |
| 28/08/1999 | Cirencester United | 1 | 2 | Cheltenham Saracens |
| 28/08/1999 | Easington Sports | 1 | 2 | Middle Barton (P) |
| 28/08/1999 | Headington Amateurs | 1 | 4 | Clanfield |
| 28/08/1999 | Old Woodstock Town (P) | 1 | 4 | Letcombe |
| 28/08/1999 | Worcester College OB | 3 | 3 | Ross Town |
| 21/08/1999 | Ardley United | 8 | 3 | Letcombe |
| 21/08/1999 | Clanfield | 0 | 4 | Worcester College OB |
| 21/08/1999 | Kidlington | 1 | 2 | Cirencester United |
| 21/08/1999 | Middle Barton (P) | 3 | 0 | Bishops Cleeve |
| 21/08/1999 | Old Woodstock Town (P) | 0 | 0 | Ross Town |
| 21/08/1999 | Purton | 0 | 0 | Headington Amateurs |
| 21/08/1999 | Wootton Bassett Town | 6 | 1 | Easington Sports |