| Dorset Combination | ||||
| Date | Home | H | A | Away |
| 16/05/2000 | Weymouth Sports | 0 | 3 | Portland United |
| 11/05/2000 | Sturminster Newton | 0 | 3 | Westland Sports |
| 10/05/2000 | Bridport Reserves | 2 | 3 | Gillingham Town |
| 09/05/2000 | Flight Refuelling | 3 | 1 | Sturminster Newton |
| 09/05/2000 | Gillingham Town | 6 | 2 | Parley Sports (-6) |
| 09/05/2000 | Shaftesbury | 0 | 6 | Bridport Reserves |
| 06/05/2000 | Bridport Reserves | 3 | 0 | Bournemouth Sports |
| 06/05/2000 | Gillingham Town | 2 | 1 | Flight Refuelling |
| 06/05/2000 | Sherborne Town | 0 | 2 | Swanage & Herston |
| 06/05/2000 | Sturminster Newton | 0 | 2 | Portland United |
| 06/05/2000 | Weymouth Sports | 1 | 4 | Wareham Rangers |
| 04/05/2000 | Hamworthy United | 2 | 0 | Blandford United |
| 04/05/2000 | Sherborne Town | 2 | 0 | Sturminster Newton |
| 04/05/2000 | Wareham Rangers | 4 | 2 | Gillingham Town |
| 04/05/2000 | Westland Sports | 4 | 1 | Allendale |
| 04/05/2000 | Weymouth Sports | 2 | 1 | Shaftesbury |
| 02/05/2000 | Bournemouth Sports | 1 | 2 | Parley Sports (-6) |
| 02/05/2000 | Bridport Reserves | 0 | 1 | Swanage & Herston |
| 02/05/2000 | Hamworthy Engineering | 5 | 1 | Gillingham Town |
| 02/05/2000 | Shaftesbury | 1 | 3 | Dorchester Town Reserves |
| 02/05/2000 | Sturminster Newton | 6 | 0 | Witchanpton United (P) |
| 02/05/2000 | Westland Sports | 3 | 2 | Weymouth Sports |
| 29/04/2000 | Allendale | 1 | 1 | Gillingham Town |
| 29/04/2000 | Blandford United | 4 | 1 | Witchanpton United (P) |
| 29/04/2000 | Dorchester Town Reserves | 0 | 1 | Portland United |
| 29/04/2000 | Flight Refuelling | 2 | 2 | Wareham Rangers |
| 29/04/2000 | Hamworthy United | 3 | 2 | Bridport Reserves |
| 29/04/2000 | Parley Sports (-6) | 2 | 1 | Shaftesbury |
| 29/04/2000 | Weymouth Sports | 0 | 1 | Sherborne Town |
| 27/04/2000 | Hamworthy Engineering | 4 | 1 | Sturminster Newton |
| 27/04/2000 | Sherborne Town | 3 | 3 | Shaftesbury |
| 25/04/2000 | Blandford United | 0 | 0 | Parley Sports (-6) |
| 25/04/2000 | Sturminster Newton | 0 | 6 | Hamworthy United |
| 25/04/2000 | Wareham Rangers | 0 | 0 | Weymouth Sports |
| 25/04/2000 | Witchanpton United (P) | 0 | 5 | Swanage & Herston |
| 22/04/2000 | Allendale | 2 | 3 | Weymouth Sports |
| 22/04/2000 | Gillingham Town | 2 | 5 | Dorchester Town Reserves |
| 22/04/2000 | Sherborne Town | 1 | 2 | Westland Sports |
| 22/04/2000 | Swanage & Herston | 5 | 0 | Parley Sports (-6) |
| 22/04/2000 | Wareham Rangers | 1 | 2 | Shaftesbury |
| 22/04/2000 | Witchanpton United (P) | 1 | 1 | Hamworthy United |
| 18/04/2000 | Allendale | 4 | 6 | Parley Sports (-6) |
| 18/04/2000 | Shaftesbury | 1 | 2 | Hamworthy United |
| 15/04/2000 | Bournemouth Sports | 4 | 0 | Hamworthy United |
| 15/04/2000 | Sturminster Newton | 0 | 1 | Wareham Rangers |
| 15/04/2000 | Weymouth Sports | 2 | 2 | Flight Refuelling |
| 15/04/2000 | Witchanpton United (P) | 2 | 3 | Hamworthy Engineering |
| 11/04/2000 | Gillingham Town | 1 | 1 | Sherborne Town |
| 11/04/2000 | Parley Sports (-6) | 4 | 3 | Hamworthy Engineering |
| 11/04/2000 | Portland United | 2 | 1 | Allendale |
| 11/04/2000 | Weymouth Sports | 2 | 2 | Swanage & Herston |
| 08/04/2000 | Allendale | 0 | 0 | Hamworthy United |
| 08/04/2000 | Flight Refuelling | 2 | 1 | Parley Sports (-6) |
| 08/04/2000 | Gillingham Town | 2 | 3 | Westland Sports |
| 08/04/2000 | Hamworthy Engineering | 1 | 6 | Portland United |
| 08/04/2000 | Sherborne Town | 0 | 0 | Bridport Reserves |
| 08/04/2000 | Swanage & Herston | 2 | 0 | Blandford United |
| 08/04/2000 | Wareham Rangers | 4 | 1 | Bournemouth Sports |
| 08/04/2000 | Weymouth Sports | 2 | 6 | Sturminster Newton |
| 08/04/2000 | Witchanpton United (P) | 1 | 3 | Shaftesbury |
| 01/04/2000 | Bournemouth Sports | 2 | 0 | Witchanpton United (P) |
| 01/04/2000 | Bridport Reserves | 1 | 1 | Blandford United |
| 01/04/2000 | Dorchester Town Reserves | 5 | 1 | Parley Sports (-6) |
| 01/04/2000 | Gillingham Town | 7 | 3 | Weymouth Sports |
| 01/04/2000 | Hamworthy United | 2 | 4 | Hamworthy Engineering |
| 01/04/2000 | Portland United | 1 | 1 | Swanage & Herston |
| 01/04/2000 | Sherborne Town | 1 | 0 | Wareham Rangers |
| 01/04/2000 | Sturminster Newton | 2 | 2 | Allendale |
| 01/04/2000 | Westland Sports | 2 | 2 | Flight Refuelling |
| 28/03/2000 | Dorchester Town Reserves | 7 | 2 | Shaftesbury |
| 28/03/2000 | Portland United | 1 | 0 | Blandford United |
| 25/03/2000 | Allendale | 0 | 1 | Sherborne Town |
| 25/03/2000 | Blandford United | 2 | 2 | Hamworthy United |
| 25/03/2000 | Bridport Reserves | 1 | 3 | Hamworthy Engineering |
| 25/03/2000 | Flight Refuelling | 0 | 3 | Dorchester Town Reserves |
| 25/03/2000 | Parley Sports (-6) | 0 | 1 | Portland United |
| 25/03/2000 | Shaftesbury | 0 | 1 | Gillingham Town |
| 25/03/2000 | Swanage & Herston | 3 | 1 | Westland Sports |
| 25/03/2000 | Weymouth Sports | 2 | 0 | Bournemouth Sports |
| 25/03/2000 | Witchanpton United (P) | 1 | 1 | Sturminster Newton |
| 21/03/2000 | Bridport Reserves | 1 | 0 | Witchanpton United (P) |
| 21/03/2000 | Shaftesbury | 0 | 3 | Parley Sports (-6) |
| 18/03/2000 | Allendale | 4 | 0 | Witchanpton United (P) |
| 18/03/2000 | Bournemouth Sports | 0 | 3 | Swanage & Herston |
| 18/03/2000 | Bridport Reserves | 2 | 1 | Portland United |
| 18/03/2000 | Gillingham Town | 4 | 2 | Hamworthy United |
| 18/03/2000 | Hamworthy Engineering | 3 | 0 | Shaftesbury |
| 18/03/2000 | Sherborne Town | 0 | 2 | Weymouth Sports |
| 18/03/2000 | Sturminster Newton | 3 | 0 | Flight Refuelling |
| 18/03/2000 | Wareham Rangers | 0 | 2 | Dorchester Town Reserves |
| 18/03/2000 | Westland Sports | 1 | 1 | Blandford United |
| 14/03/2000 | Parley Sports (-6) | 3 | 0 | Witchanpton United (P) |
| 14/03/2000 | Shaftesbury | 0 | 1 | Sturminster Newton |
| 14/03/2000 | Swanage & Herston | 3 | 0 | Flight Refuelling |
| 11/03/2000 | Blandford United | 1 | 2 | Hamworthy Engineering |
| 11/03/2000 | Bridport Reserves | 1 | 2 | Flight Refuelling |
| 11/03/2000 | Hamworthy United | 3 | 1 | Sherborne Town |
| 11/03/2000 | Parley Sports (-6) | 0 | 0 | Allendale |
| 11/03/2000 | Portland United | 0 | 0 | Bournemouth Sports |
| 11/03/2000 | Shaftesbury | 2 | 1 | Wareham Rangers |
| 11/03/2000 | Swanage & Herston | 2 | 1 | Sturminster Newton |
| 11/03/2000 | Weymouth Sports | 1 | 1 | Westland Sports |
| 11/03/2000 | Witchanpton United (P) | 1 | 2 | Gillingham Town |
| 04/03/2000 | Allendale | 3 | 2 | Shaftesbury |
| 04/03/2000 | Flight Refuelling | 3 | 0 | Bournemouth Sports |
| 04/03/2000 | Gillingham Town | 1 | 6 | Portland United |
| 04/03/2000 | Hamworthy Engineering | 3 | 1 | Hamworthy United |
| 04/03/2000 | Sherborne Town | 0 | 2 | Parley Sports (-6) |
| 04/03/2000 | Wareham Rangers | 1 | 6 | Bridport Reserves |
| 04/03/2000 | Westland Sports | 0 | 4 | Swanage & Herston |
| 04/03/2000 | Weymouth Sports | 0 | 3 | Blandford United |
| 26/02/2000 | Blandford United | 0 | 1 | Allendale |
| 26/02/2000 | Bridport Reserves | 3 | 1 | Weymouth Sports |
| 26/02/2000 | Hamworthy Engineering | 4 | 4 | Parley Sports (-6) |
| 26/02/2000 | Hamworthy United | 1 | 0 | Westland Sports |
| 26/02/2000 | Shaftesbury | 2 | 2 | Bournemouth Sports |
| 26/02/2000 | Sherborne Town | 2 | 1 | Flight Refuelling |
| 26/02/2000 | Sturminster Newton | 1 | 3 | Gillingham Town |
| 26/02/2000 | Swanage & Herston | 0 | 1 | Dorchester Town Reserves |
| 26/02/2000 | Witchanpton United (P) | 1 | 2 | Wareham Rangers |
| 23/02/2000 | Portland United | 4 | 1 | Hamworthy Engineering |
| 22/02/2000 | Bridport Reserves | 2 | 0 | Allendale |
| 19/02/2000 | Allendale | 0 | 1 | Swanage & Herston |
| 19/02/2000 | Bournemouth Sports | 1 | 8 | Dorchester Town Reserves |
| 19/02/2000 | Flight Refuelling | 0 | 0 | Shaftesbury |
| 19/02/2000 | Gillingham Town | 3 | 2 | Blandford United |
| 19/02/2000 | Hamworthy Engineering | 3 | 1 | Weymouth Sports |
| 19/02/2000 | Parley Sports (-6) | 5 | 2 | Westland Sports |
| 19/02/2000 | Portland United | 3 | 0 | Bridport Reserves |
| 19/02/2000 | Wareham Rangers | 2 | 2 | Sturminster Newton |
| 19/02/2000 | Witchanpton United (P) | 1 | 2 | Sherborne Town |
| 15/02/2000 | Swanage & Herston | 2 | 1 | Hamworthy Engineering |
| 12/02/2000 | Allendale | 4 | 3 | Bournemouth Sports |
| 12/02/2000 | Blandford United | 4 | 1 | Flight Refuelling |
| 12/02/2000 | Dorchester Town Reserves | 0 | 1 | Witchanpton United (P) |
| 12/02/2000 | Hamworthy United | 2 | 1 | Weymouth Sports |
| 12/02/2000 | Swanage & Herston | 4 | 0 | Shaftesbury |
| 12/02/2000 | Westland Sports | 2 | 2 | Hamworthy Engineering |
| 05/02/2000 | Bournemouth Sports | 0 | 2 | Sturminster Newton |
| 05/02/2000 | Bridport Reserves | 1 | 0 | Hamworthy United |
| 05/02/2000 | Flight Refuelling | 6 | 3 | Swanage & Herston |
| 05/02/2000 | Hamworthy Engineering | 3 | 4 | Dorchester Town Reserves |
| 05/02/2000 | Parley Sports (-6) | 2 | 1 | Blandford United |
| 05/02/2000 | Portland United | 5 | 0 | Sherborne Town |
| 05/02/2000 | Shaftesbury | 1 | 2 | Westland Sports |
| 05/02/2000 | Wareham Rangers | 0 | 4 | Allendale |
| 01/02/2000 | Dorchester Town Reserves | 3 | 1 | Hamworthy United |
| 29/01/2000 | Allendale | 3 | 4 | Hamworthy Engineering |
| 29/01/2000 | Blandford United | 2 | 0 | Dorchester Town Reserves |
| 29/01/2000 | Gillingham Town | 1 | 1 | Shaftesbury |
| 29/01/2000 | Hamworthy United | 3 | 2 | Flight Refuelling |
| 29/01/2000 | Parley Sports (-6) | 2 | 1 | Wareham Rangers |
| 29/01/2000 | Sherborne Town | 2 | 0 | Bournemouth Sports |
| 29/01/2000 | Sturminster Newton | 2 | 3 | Bridport Reserves |
| 29/01/2000 | Westland Sports | 1 | 5 | Portland United |
| 29/01/2000 | Witchanpton United (P) | 0 | 2 | Weymouth Sports |
| 22/01/2000 | Dorchester Town Reserves | 1 | 1 | Sherborne Town |
| 22/01/2000 | Flight Refuelling | 0 | 1 | Allendale |
| 22/01/2000 | Hamworthy Engineering | 4 | 0 | Bournemouth Sports |
| 22/01/2000 | Wareham Rangers | 0 | 3 | Hamworthy United |
| 22/01/2000 | Witchanpton United (P) | 0 | 4 | Westland Sports |
| 15/01/2000 | Bournemouth Sports | 1 | 4 | Blandford United |
| 15/01/2000 | Bridport Reserves | 3 | 2 | Sturminster Newton |
| 15/01/2000 | Gillingham Town | 3 | 2 | Swanage & Herston |
| 15/01/2000 | Hamworthy Engineering | 3 | 0 | Wareham Rangers |
| 15/01/2000 | Hamworthy United | 5 | 0 | Witchanpton United (P) |
| 15/01/2000 | Parley Sports (-6) | 2 | 1 | Dorchester Town Reserves |
| 15/01/2000 | Portland United | 3 | 0 | Flight Refuelling |
| 15/01/2000 | Shaftesbury | 0 | 4 | Sherborne Town |
| 15/01/2000 | Weymouth Sports | 1 | 3 | Allendale |
| 08/01/2000 | Allendale | 1 | 3 | Dorchester Town Reserves |
| 08/01/2000 | Blandford United | 3 | 2 | Portland United |
| 08/01/2000 | Gillingham Town | 0 | 0 | Bridport Reserves |
| 08/01/2000 | Sherborne Town | 1 | 5 | Hamworthy Engineering |
| 08/01/2000 | Sturminster Newton | 0 | 4 | Swanage & Herston |
| 08/01/2000 | Westland Sports | 2 | 0 | Bournemouth Sports |
| 08/01/2000 | Weymouth Sports | 0 | 0 | Hamworthy United |
| 08/01/2000 | Witchanpton United (P) | 0 | 5 | Flight Refuelling |
| 18/12/1999 | Bournemouth Sports | 2 | 4 | Portland United |
| 18/12/1999 | Dorchester Town Reserves | 2 | 1 | Flight Refuelling |
| 18/12/1999 | Hamworthy Engineering | 5 | 0 | Witchanpton United (P) |
| 18/12/1999 | Hamworthy United | 3 | 2 | Parley Sports (-6) |
| 18/12/1999 | Sturminster Newton | 0 | 0 | Blandford United |
| 18/12/1999 | Wareham Rangers | 2 | 1 | Westland Sports |
| 18/12/1999 | Weymouth Sports | 1 | 2 | Gillingham Town |
| 11/12/1999 | Blandford United | 2 | 1 | Wareham Rangers |
| 11/12/1999 | Bournemouth Sports | 2 | 7 | Allendale |
| 11/12/1999 | Parley Sports (-6) | 4 | 1 | Sherborne Town |
| 11/12/1999 | Portland United | 7 | 0 | Witchanpton United (P) |
| 11/12/1999 | Westland Sports | 2 | 1 | Bridport Reserves |
| 04/12/1999 | Shaftesbury | 0 | 2 | Portland United |
| 04/12/1999 | Sherborne Town | 1 | 8 | Dorchester Town Reserves |
| 04/12/1999 | Sturminster Newton | 2 | 0 | Hamworthy Engineering |
| 04/12/1999 | Wareham Rangers | 2 | 2 | Swanage & Herston |
| 04/12/1999 | Witchanpton United (P) | 0 | 6 | Blandford United |
| 27/11/1999 | Allendale | 0 | 1 | Bridport Reserves |
| 27/11/1999 | Blandford United | 2 | 1 | Sherborne Town |
| 27/11/1999 | Bournemouth Sports | 0 | 9 | Gillingham Town |
| 27/11/1999 | Dorchester Town Reserves | 2 | 1 | Sturminster Newton |
| 27/11/1999 | Flight Refuelling | 1 | 2 | Hamworthy Engineering |
| 27/11/1999 | Parley Sports (-6) | 6 | 1 | Weymouth Sports |
| 27/11/1999 | Portland United | 4 | 0 | Wareham Rangers |
| 27/11/1999 | Shaftesbury | 3 | 1 | Witchanpton United (P) |
| 27/11/1999 | Swanage & Herston | 0 | 1 | Hamworthy United |
| 20/11/1999 | Bridport Reserves | 3 | 1 | Shaftesbury |
| 20/11/1999 | Gillingham Town | 4 | 1 | Allendale |
| 20/11/1999 | Hamworthy Engineering | 1 | 2 | Blandford United |
| 20/11/1999 | Hamworthy United | 2 | 0 | Bournemouth Sports |
| 20/11/1999 | Sherborne Town | 1 | 3 | Portland United |
| 20/11/1999 | Wareham Rangers | 0 | 0 | Flight Refuelling |
| 20/11/1999 | Westland Sports | 1 | 3 | Parley Sports (-6) |
| 20/11/1999 | Weymouth Sports | 0 | 1 | Dorchester Town Reserves |
| 13/11/1999 | Allendale | 1 | 0 | Westland Sports |
| 13/11/1999 | Blandford United | 4 | 3 | Shaftesbury |
| 13/11/1999 | Bournemouth Sports | 1 | 3 | Bridport Reserves |
| 13/11/1999 | Dorchester Town Reserves | 5 | 0 | Gillingham Town |
| 13/11/1999 | Flight Refuelling | 7 | 1 | Sherborne Town |
| 13/11/1999 | Swanage & Herston | 0 | 0 | Portland United |
| 06/11/1999 | Dorchester Town Reserves | 2 | 1 | Bridport Reserves |
| 30/10/1999 | Allendale | 2 | 2 | Portland United |
| 30/10/1999 | Blandford United | 2 | 0 | Gillingham Town |
| 30/10/1999 | Bournemouth Sports | 1 | 5 | Wareham Rangers |
| 30/10/1999 | Hamworthy Engineering | 2 | 0 | Bridport Reserves |
| 30/10/1999 | Hamworthy United | 2 | 1 | Sturminster Newton |
| 30/10/1999 | Parley Sports (-6) | 3 | 0 | Swanage & Herston |
| 30/10/1999 | Westland Sports | 1 | 1 | Dorchester Town Reserves |
| 23/10/1999 | Allendale | 0 | 0 | Blandford United |
| 23/10/1999 | Flight Refuelling | 4 | 2 | Hamworthy United |
| 20/10/1999 | Portland United | 2 | 0 | Hamworthy United |
| 19/10/1999 | Dorchester Town Reserves | 3 | 0 | Westland Sports |
| 16/10/1999 | Allendale | 1 | 1 | Flight Refuelling |
| 16/10/1999 | Blandford United | 0 | 1 | Weymouth Sports |
| 16/10/1999 | Hamworthy United | 0 | 3 | Gillingham Town |
| 16/10/1999 | Parley Sports (-6) | 3 | 1 | Bridport Reserves |
| 16/10/1999 | Portland United | 4 | 0 | Dorchester Town Reserves |
| 16/10/1999 | Shaftesbury | 0 | 1 | Swanage & Herston |
| 16/10/1999 | Sturminster Newton | 5 | 0 | Bournemouth Sports |
| 16/10/1999 | Wareham Rangers | 2 | 2 | Sherborne Town |
| 16/10/1999 | Westland Sports | 0 | 0 | Witchanpton United (P) |
| 12/10/1999 | Bridport Reserves | 2 | 2 | Sherborne Town |
| 12/10/1999 | Swanage & Herston | 2 | 0 | Wareham Rangers |
| 09/10/1999 | Bournemouth Sports | 1 | 4 | Shaftesbury |
| 09/10/1999 | Dorchester Town Reserves | 0 | 1 | Allendale |
| 09/10/1999 | Flight Refuelling | 2 | 1 | Blandford United |
| 09/10/1999 | Gillingham Town | 0 | 2 | Sturminster Newton |
| 09/10/1999 | Swanage & Herston | 6 | 0 | Sherborne Town |
| 09/10/1999 | Westland Sports | 3 | 1 | Wareham Rangers |
| 09/10/1999 | Weymouth Sports | 1 | 13 | Hamworthy Engineering |
| 09/10/1999 | Witchanpton United (P) | 2 | 6 | Portland United |
| 02/10/1999 | Blandford United | 0 | 2 | Bridport Reserves |
| 02/10/1999 | Bournemouth Sports | 2 | 2 | Sherborne Town |
| 02/10/1999 | Hamworthy Engineering | 2 | 6 | Westland Sports |
| 02/10/1999 | Hamworthy United | 1 | 3 | Wareham Rangers |
| 02/10/1999 | Portland United | 2 | 1 | Gillingham Town |
| 02/10/1999 | Sturminster Newton | 1 | 2 | Parley Sports (-6) |
| 02/10/1999 | Witchanpton United (P) | 0 | 9 | Dorchester Town Reserves |
| 28/09/1999 | Shaftesbury | 0 | 6 | Weymouth Sports |
| 25/09/1999 | Flight Refuelling | 5 | 2 | Portland United |
| 25/09/1999 | Gillingham Town | 3 | 0 | Bournemouth Sports |
| 25/09/1999 | Parley Sports (-6) | 5 | 2 | Sturminster Newton |
| 25/09/1999 | Swanage & Herston | 3 | 0 | Witchanpton United (P) |
| 25/09/1999 | Wareham Rangers | 0 | 2 | Hamworthy Engineering |
| 25/09/1999 | Westland Sports | 2 | 2 | Hamworthy United |
| 18/09/1999 | Allendale | 2 | 0 | Wareham Rangers |
| 18/09/1999 | Blandford United | 4 | 0 | Westland Sports |
| 18/09/1999 | Bournemouth Sports | 2 | 10 | Flight Refuelling |
| 18/09/1999 | Hamworthy Engineering | 1 | 0 | Swanage & Herston |
| 18/09/1999 | Hamworthy United | 0 | 1 | Dorchester Town Reserves |
| 18/09/1999 | Parley Sports (-6) | 2 | 2 | Gillingham Town |
| 18/09/1999 | Portland United | 1 | 2 | Shaftesbury |
| 18/09/1999 | Sturminster Newton | 2 | 0 | Weymouth Sports |
| 18/09/1999 | Witchanpton United (P) | 2 | 4 | Bridport Reserves |
| 11/09/1999 | Dorchester Town Reserves | 3 | 2 | Hamworthy Engineering |
| 11/09/1999 | Flight Refuelling | 2 | 2 | Gillingham Town |
| 11/09/1999 | Portland United | 1 | 0 | Parley Sports (-6) |
| 11/09/1999 | Sherborne Town | 0 | 3 | Hamworthy United |
| 11/09/1999 | Swanage & Herston | 2 | 1 | Allendale |
| 11/09/1999 | Wareham Rangers | 3 | 3 | Blandford United |
| 11/09/1999 | Westland Sports | 4 | 2 | Sturminster Newton |
| 11/09/1999 | Weymouth Sports | 1 | 1 | Bridport Reserves |
| 11/09/1999 | Witchanpton United (P) | 6 | 3 | Bournemouth Sports |
| 07/09/1999 | Dorchester Town Reserves | 3 | 0 | Weymouth Sports |
| 04/09/1999 | Allendale | 0 | 1 | Sturminster Newton |
| 04/09/1999 | Blandford United | 0 | 2 | Swanage & Herston |
| 04/09/1999 | Bournemouth Sports | 2 | 3 | Weymouth Sports |
| 04/09/1999 | Bridport Reserves | 0 | 3 | Westland Sports |
| 04/09/1999 | Dorchester Town Reserves | 4 | 0 | Wareham Rangers |
| 04/09/1999 | Gillingham Town | 3 | 2 | Witchanpton United (P) |
| 04/09/1999 | Hamworthy Engineering | 5 | 1 | Sherborne Town |
| 04/09/1999 | Hamworthy United | 3 | 0 | Shaftesbury |
| 04/09/1999 | Parley Sports (-6) | 2 | 2 | Flight Refuelling |
| 31/08/1999 | Bridport Reserves | 0 | 1 | Wareham Rangers |
| 31/08/1999 | Dorchester Town Reserves | 4 | 2 | Bournemouth Sports |
| 31/08/1999 | Hamworthy United | 2 | 2 | Allendale |
| 31/08/1999 | Shaftesbury | 0 | 3 | Flight Refuelling |
| 31/08/1999 | Sturminster Newton | 5 | 0 | Sherborne Town |
| 31/08/1999 | Swanage & Herston | 4 | 4 | Weymouth Sports |
| 31/08/1999 | Westland Sports | 1 | 7 | Gillingham Town |
| 31/08/1999 | Witchanpton United (P) | 0 | 8 | Parley Sports (-6) |
| 28/08/1999 | Bournemouth Sports | 1 | 7 | Hamworthy Engineering |
| 28/08/1999 | Flight Refuelling | 1 | 4 | Bridport Reserves |
| 28/08/1999 | Portland United | 5 | 0 | Westland Sports |
| 28/08/1999 | Shaftesbury | 2 | 4 | Allendale |
| 28/08/1999 | Sherborne Town | 0 | 4 | Blandford United |
| 28/08/1999 | Sturminster Newton | 1 | 2 | Dorchester Town Reserves |
| 28/08/1999 | Swanage & Herston | 2 | 1 | Gillingham Town |
| 28/08/1999 | Wareham Rangers | 4 | 1 | Parley Sports (-6) |
| 28/08/1999 | Weymouth Sports | 3 | 0 | Witchanpton United (P) |
| 26/08/1999 | Sherborne Town | 0 | 0 | Gillingham Town |
| 24/08/1999 | Blandford United | 2 | 1 | Sturminster Newton |
| 24/08/1999 | Dorchester Town Reserves | 1 | 4 | Swanage & Herston |
| 24/08/1999 | Flight Refuelling | 0 | 0 | Witchanpton United (P) |
| 24/08/1999 | Hamworthy Engineering | 2 | 2 | Allendale |
| 24/08/1999 | Parley Sports (-6) | 9 | 0 | Bournemouth Sports |
| 24/08/1999 | Portland United | 1 | 0 | Weymouth Sports |
| 24/08/1999 | Westland Sports | 2 | 1 | Shaftesbury |
| 21/08/1999 | Bridport Reserves | 0 | 2 | Dorchester Town Reserves |
| 21/08/1999 | Flight Refuelling | 5 | 3 | Westland Sports |
| 21/08/1999 | Gillingham Town | 3 | 4 | Hamworthy Engineering |
| 21/08/1999 | Hamworthy United | 2 | 2 | Portland United |
| 21/08/1999 | Shaftesbury | 1 | 2 | Blandford United |
| 21/08/1999 | Sherborne Town | 1 | 4 | Allendale |
| 21/08/1999 | Swanage & Herston | 3 | 0 | Bournemouth Sports |
| 21/08/1999 | Wareham Rangers | 1 | 0 | Witchanpton United (P) |
| 21/08/1999 | Weymouth Sports | 2 | 4 | Parley Sports (-6) |
| 17/08/1999 | Blandford United | 3 | 0 | Bournemouth Sports |
| 17/08/1999 | Hamworthy Engineering | 3 | 4 | Flight Refuelling |
| 17/08/1999 | Parley Sports (-6) | 2 | 0 | Hamworthy United |
| 17/08/1999 | Sturminster Newton | 3 | 0 | Shaftesbury |
| 17/08/1999 | Swanage & Herston | 1 | 1 | Bridport Reserves |
| 17/08/1999 | Wareham Rangers | 1 | 3 | Portland United |
| 17/08/1999 | Westland Sports | 3 | 1 | Sherborne Town |
| 17/08/1999 | Witchanpton United (P) | 0 | 3 | Allendale |
| 14/08/1999 | Bournemouth Sports | 1 | 6 | Westland Sports |
| 14/08/1999 | Bridport Reserves | 1 | 3 | Parley Sports (-6) |
| 14/08/1999 | Dorchester Town Reserves | 3 | 0 | Blandford United |
| 14/08/1999 | Flight Refuelling | 4 | 2 | Weymouth Sports |
| 14/08/1999 | Gillingham Town | 2 | 2 | Wareham Rangers |
| 14/08/1999 | Hamworthy United | 1 | 1 | Swanage & Herston |
| 14/08/1999 | Portland United | 3 | 1 | Sturminster Newton |
| 14/08/1999 | Shaftesbury | 1 | 3 | Hamworthy Engineering |
| 14/08/1999 | Sherborne Town | 3 | 3 | Witchanpton United (P) |