| Wessex | ||||
| Date | Home | H | A | Away |
| 01/05/2000 | AFC Totton | 1 | 3 | Fareham Town |
| 01/05/2000 | Brockenhurst | 1 | 6 | Cowes Sports |
| 29/04/2000 | AFC Totton | 2 | 0 | Christchurch |
| 29/04/2000 | BAT Sports | 7 | 3 | Fareham Town |
| 29/04/2000 | Bemerton Heath H | 2 | 2 | Andover (R) |
| 29/04/2000 | Bournemouth (-2) | 1 | 4 | Downton |
| 29/04/2000 | Brockenhurst | 0 | 5 | Eastleigh |
| 29/04/2000 | East Cowes Victoria | 1 | 8 | Lymington & New Milt |
| 29/04/2000 | Gosport Borough | 1 | 2 | Cowes Sports |
| 29/04/2000 | Hamble Aerostructure | 1 | 4 | Wimborne Town |
| 29/04/2000 | Whitchurch United | 0 | 3 | Moneyfields |
| 26/04/2000 | AFC Newbury | 6 | 0 | Brockenhurst |
| 26/04/2000 | Christchurch | 1 | 3 | AFC Totton |
| 26/04/2000 | Eastleigh | 1 | 0 | Bournemouth (-2) |
| 26/04/2000 | Fareham Town | 1 | 0 | Cowes Sports |
| 24/04/2000 | AFC Totton | 0 | 1 | BAT Sports |
| 24/04/2000 | Andover (R) | 2 | 1 | Whitchurch United |
| 24/04/2000 | Christchurch | 2 | 1 | Bournemouth (-2) |
| 24/04/2000 | Cowes Sports | 4 | 1 | East Cowes Victoria |
| 24/04/2000 | Downton | 2 | 1 | Bemerton Heath H |
| 24/04/2000 | Eastleigh | 5 | 0 | Hamble Aerostructure |
| 24/04/2000 | Fareham Town | 1 | 1 | Gosport Borough |
| 24/04/2000 | Lymington & New Milt | 6 | 0 | Brockenhurst |
| 24/04/2000 | Moneyfields | 1 | 1 | Portsmouth RN |
| 24/04/2000 | Thatcham Town | 0 | 0 | AFC Newbury |
| 22/04/2000 | AFC Totton | 4 | 1 | Downton |
| 22/04/2000 | BAT Sports | 2 | 0 | Cowes Sports |
| 22/04/2000 | Bemerton Heath H | 1 | 4 | Moneyfields |
| 22/04/2000 | Bournemouth (-2) | 2 | 8 | Andover (R) |
| 22/04/2000 | Brockenhurst | 0 | 9 | Wimborne Town |
| 22/04/2000 | Christchurch | 5 | 2 | Fareham Town |
| 22/04/2000 | East Cowes Victoria | 0 | 5 | Eastleigh |
| 22/04/2000 | Gosport Borough | 0 | 4 | Lymington & New Milt |
| 22/04/2000 | Portsmouth RN | 1 | 3 | AFC Newbury |
| 22/04/2000 | Whitchurch United | 1 | 2 | Thatcham Town |
| 20/04/2000 | Bournemouth (-2) | 1 | 2 | Thatcham Town |
| 15/04/2000 | Andover (R) | 3 | 4 | BAT Sports |
| 15/04/2000 | Cowes Sports | 0 | 2 | AFC Totton |
| 15/04/2000 | Downton | 1 | 1 | Christchurch |
| 15/04/2000 | Hamble Aerostructure | 0 | 0 | Portsmouth RN |
| 15/04/2000 | Lymington & New Milt | 1 | 1 | Bournemouth (-2) |
| 15/04/2000 | Moneyfields | 2 | 1 | Gosport Borough |
| 15/04/2000 | Thatcham Town | 5 | 0 | East Cowes Victoria |
| 15/04/2000 | Wimborne Town | 2 | 1 | Whitchurch United |
| 13/04/2000 | East Cowes Victoria | 3 | 5 | AFC Totton |
| 13/04/2000 | Wimborne Town | 7 | 1 | Bournemouth (-2) |
| 11/04/2000 | Bournemouth (-2) | 2 | 2 | AFC Newbury |
| 11/04/2000 | Brockenhurst | 0 | 4 | AFC Totton |
| 11/04/2000 | Downton | 3 | 2 | Gosport Borough |
| 11/04/2000 | Eastleigh | 0 | 0 | Bemerton Heath H |
| 11/04/2000 | Lymington & New Milt | 3 | 2 | Andover (R) |
| 10/04/2000 | Portsmouth RN | 2 | 2 | Thatcham Town |
| 08/04/2000 | AFC Totton | 0 | 2 | Andover (R) |
| 08/04/2000 | BAT Sports | 0 | 2 | Lymington & New Milt |
| 08/04/2000 | Bemerton Heath H | 1 | 2 | Thatcham Town |
| 08/04/2000 | Bournemouth (-2) | 1 | 2 | Moneyfields |
| 08/04/2000 | Brockenhurst | 1 | 1 | Hamble Aerostructure |
| 08/04/2000 | Christchurch | 2 | 0 | Cowes Sports |
| 08/04/2000 | East Cowes Victoria | 0 | 2 | Wimborne Town |
| 08/04/2000 | Fareham Town | 3 | 3 | Downton |
| 08/04/2000 | Gosport Borough | 0 | 1 | Eastleigh |
| 08/04/2000 | Whitchurch United | 1 | 1 | AFC Newbury |
| 06/04/2000 | AFC Totton | 0 | 1 | Eastleigh |
| 05/04/2000 | Fareham Town | 0 | 2 | AFC Newbury |
| 04/04/2000 | Brockenhurst | 1 | 2 | Lymington & New Milt |
| 04/04/2000 | Downton | 2 | 3 | Wimborne Town |
| 04/04/2000 | Thatcham Town | 2 | 3 | Andover (R) |
| 01/04/2000 | AFC Newbury | 3 | 1 | East Cowes Victoria |
| 01/04/2000 | Andover (R) | 7 | 1 | Christchurch |
| 01/04/2000 | Cowes Sports | 2 | 2 | Fareham Town |
| 01/04/2000 | Hamble Aerostructure | 5 | 2 | Whitchurch United |
| 01/04/2000 | Lymington & New Milt | 1 | 1 | AFC Totton |
| 01/04/2000 | Moneyfields | 2 | 1 | BAT Sports |
| 01/04/2000 | Portsmouth RN | 2 | 2 | Brockenhurst |
| 01/04/2000 | Thatcham Town | 2 | 0 | Gosport Borough |
| 01/04/2000 | Wimborne Town | 3 | 0 | Bemerton Heath H |
| 29/03/2000 | Cowes Sports | 1 | 1 | Thatcham Town |
| 29/03/2000 | Fareham Town | 2 | 0 | Whitchurch United |
| 28/03/2000 | AFC Totton | 6 | 0 | Portsmouth RN |
| 28/03/2000 | Christchurch | 0 | 0 | Hamble Aerostructure |
| 25/03/2000 | AFC Totton | 0 | 0 | Moneyfields |
| 25/03/2000 | BAT Sports | 1 | 0 | Eastleigh |
| 25/03/2000 | Bemerton Heath H | 3 | 2 | AFC Newbury |
| 25/03/2000 | Christchurch | 1 | 3 | Lymington & New Milt |
| 25/03/2000 | Downton | 1 | 1 | Cowes Sports |
| 25/03/2000 | East Cowes Victoria | 1 | 3 | Hamble Aerostructure |
| 25/03/2000 | Fareham Town | 4 | 4 | Andover (R) |
| 25/03/2000 | Gosport Borough | 0 | 0 | Wimborne Town |
| 25/03/2000 | Whitchurch United | 0 | 0 | Portsmouth RN |
| 22/03/2000 | Fareham Town | 2 | 1 | BAT Sports |
| 21/03/2000 | Hamble Aerostructure | 0 | 0 | Cowes Sports |
| 18/03/2000 | AFC Newbury | 1 | 0 | Gosport Borough |
| 18/03/2000 | Andover (R) | 4 | 2 | Downton |
| 18/03/2000 | Brockenhurst | 1 | 1 | Whitchurch United |
| 18/03/2000 | Eastleigh | 1 | 1 | AFC Totton |
| 18/03/2000 | Fareham Town | 0 | 3 | Lymington & New Milt |
| 18/03/2000 | Hamble Aerostructure | 0 | 0 | Bemerton Heath H |
| 18/03/2000 | Moneyfields | 2 | 0 | Christchurch |
| 18/03/2000 | Portsmouth RN | 4 | 1 | East Cowes Victoria |
| 18/03/2000 | Thatcham Town | 2 | 6 | BAT Sports |
| 14/03/2000 | AFC Newbury | 0 | 0 | Cowes Sports |
| 14/03/2000 | Bemerton Heath H | 0 | 4 | Lymington & New Milt |
| 14/03/2000 | Christchurch | 0 | 0 | East Cowes Victoria |
| 13/03/2000 | Portsmouth RN | 0 | 2 | Andover (R) |
| 11/03/2000 | AFC Totton | 2 | 1 | Thatcham Town |
| 11/03/2000 | BAT Sports | 0 | 3 | Wimborne Town |
| 11/03/2000 | Bemerton Heath H | 4 | 1 | Portsmouth RN |
| 11/03/2000 | Christchurch | 0 | 1 | Eastleigh |
| 11/03/2000 | Cowes Sports | 1 | 1 | Andover (R) |
| 11/03/2000 | Downton | 0 | 4 | Lymington & New Milt |
| 11/03/2000 | East Cowes Victoria | 4 | 1 | Brockenhurst |
| 11/03/2000 | Fareham Town | 0 | 0 | Moneyfields |
| 11/03/2000 | Gosport Borough | 2 | 0 | Hamble Aerostructure |
| 07/03/2000 | Christchurch | 0 | 1 | Gosport Borough |
| 07/03/2000 | Downton | 0 | 2 | Bournemouth (-2) |
| 07/03/2000 | East Cowes Victoria | 2 | 2 | Fareham Town |
| 04/03/2000 | AFC Newbury | 3 | 3 | BAT Sports |
| 04/03/2000 | Brockenhurst | 1 | 5 | Bemerton Heath H |
| 04/03/2000 | Eastleigh | 4 | 1 | Fareham Town |
| 04/03/2000 | Hamble Aerostructure | 1 | 1 | Bournemouth (-2) |
| 04/03/2000 | Lymington & New Milt | 2 | 0 | Cowes Sports |
| 04/03/2000 | Moneyfields | 2 | 0 | Downton |
| 04/03/2000 | Portsmouth RN | 2 | 2 | Gosport Borough |
| 04/03/2000 | Thatcham Town | 0 | 1 | Christchurch |
| 04/03/2000 | Whitchurch United | 5 | 0 | East Cowes Victoria |
| 04/03/2000 | Wimborne Town | 1 | 1 | AFC Totton |
| 29/02/2000 | Thatcham Town | 0 | 3 | Wimborne Town |
| 29/02/2000 | Whitchurch United | 3 | 6 | Andover (R) |
| 26/02/2000 | AFC Totton | 2 | 0 | AFC Newbury |
| 26/02/2000 | Andover (R) | 1 | 1 | Lymington & New Milt |
| 26/02/2000 | BAT Sports | 2 | 1 | Hamble Aerostructure |
| 26/02/2000 | Bemerton Heath H | 3 | 1 | Whitchurch United |
| 26/02/2000 | Bournemouth (-2) | 5 | 1 | Portsmouth RN |
| 26/02/2000 | Christchurch | 0 | 1 | Wimborne Town |
| 26/02/2000 | Cowes Sports | 3 | 1 | Moneyfields |
| 26/02/2000 | Downton | 2 | 0 | Eastleigh |
| 26/02/2000 | Fareham Town | 1 | 1 | Thatcham Town |
| 26/02/2000 | Gosport Borough | 2 | 1 | Brockenhurst |
| 19/02/2000 | AFC Newbury | 5 | 0 | Christchurch |
| 19/02/2000 | Brockenhurst | 2 | 0 | Bournemouth (-2) |
| 19/02/2000 | East Cowes Victoria | 0 | 2 | Bemerton Heath H |
| 19/02/2000 | Eastleigh | 1 | 0 | Cowes Sports |
| 19/02/2000 | Hamble Aerostructure | 0 | 2 | AFC Totton |
| 19/02/2000 | Moneyfields | 4 | 0 | Andover (R) |
| 19/02/2000 | Portsmouth RN | 0 | 2 | BAT Sports |
| 19/02/2000 | Thatcham Town | 2 | 1 | Downton |
| 19/02/2000 | Whitchurch United | 1 | 0 | Gosport Borough |
| 19/02/2000 | Wimborne Town | 2 | 2 | Fareham Town |
| 15/02/2000 | BAT Sports | 9 | 1 | Downton |
| 15/02/2000 | Cowes Sports | 3 | 2 | Christchurch |
| 12/02/2000 | Andover (R) | 5 | 0 | Eastleigh |
| 12/02/2000 | BAT Sports | 4 | 1 | Brockenhurst |
| 12/02/2000 | Bournemouth (-2) | 2 | 2 | Whitchurch United |
| 12/02/2000 | Gosport Borough | 7 | 1 | East Cowes Victoria |
| 12/02/2000 | Lymington & New Milt | 4 | 0 | Moneyfields |
| 08/02/2000 | Christchurch | 1 | 3 | Moneyfields |
| 05/02/2000 | AFC Newbury | 1 | 1 | Downton |
| 05/02/2000 | Bemerton Heath H | 4 | 2 | Gosport Borough |
| 05/02/2000 | East Cowes Victoria | 1 | 5 | Bournemouth (-2) |
| 05/02/2000 | Eastleigh | 1 | 2 | Lymington & New Milt |
| 05/02/2000 | Hamble Aerostructure | 1 | 1 | Fareham Town |
| 05/02/2000 | Portsmouth RN | 1 | 3 | Christchurch |
| 05/02/2000 | Whitchurch United | 2 | 3 | BAT Sports |
| 05/02/2000 | Wimborne Town | 2 | 1 | Cowes Sports |
| 02/02/2000 | Cowes Sports | 1 | 1 | Gosport Borough |
| 02/02/2000 | Fareham Town | 2 | 0 | Bemerton Heath H |
| 01/02/2000 | AFC Totton | 2 | 2 | Lymington & New Milt |
| 01/02/2000 | Downton | 8 | 1 | East Cowes Victoria |
| 01/02/2000 | Wimborne Town | 2 | 0 | Eastleigh |
| 31/01/2000 | Portsmouth RN | 0 | 1 | Moneyfields |
| 29/01/2000 | AFC Totton | 0 | 0 | Whitchurch United |
| 29/01/2000 | Andover (R) | 0 | 3 | Wimborne Town |
| 29/01/2000 | BAT Sports | 4 | 0 | East Cowes Victoria |
| 29/01/2000 | Bournemouth (-2) | 0 | 3 | Bemerton Heath H |
| 29/01/2000 | Christchurch | 3 | 1 | Brockenhurst |
| 29/01/2000 | Cowes Sports | 1 | 1 | AFC Newbury |
| 29/01/2000 | Downton | 2 | 4 | Hamble Aerostructure |
| 29/01/2000 | Fareham Town | 0 | 0 | Portsmouth RN |
| 29/01/2000 | Lymington & New Milt | 4 | 1 | Thatcham Town |
| 29/01/2000 | Moneyfields | 0 | 3 | Eastleigh |
| 22/01/2000 | AFC Newbury | 1 | 0 | Andover (R) |
| 22/01/2000 | Bemerton Heath H | 0 | 0 | BAT Sports |
| 22/01/2000 | Brockenhurst | 1 | 2 | Fareham Town |
| 22/01/2000 | Gosport Borough | 1 | 0 | Bournemouth (-2) |
| 22/01/2000 | Portsmouth RN | 6 | 3 | Downton |
| 22/01/2000 | Thatcham Town | 2 | 2 | Moneyfields |
| 22/01/2000 | Whitchurch United | 2 | 2 | Christchurch |
| 22/01/2000 | Wimborne Town | 2 | 0 | Lymington & New Milt |
| 19/01/2000 | Moneyfields | 5 | 3 | Brockenhurst |
| 18/01/2000 | Bournemouth (-2) | 0 | 4 | Wimborne Town |
| 18/01/2000 | Christchurch | 0 | 5 | Andover (R) |
| 18/01/2000 | Gosport Borough | 0 | 3 | AFC Totton |
| 18/01/2000 | Lymington & New Milt | 2 | 0 | Fareham Town |
| 18/01/2000 | Whitchurch United | 1 | 5 | Bemerton Heath H |
| 15/01/2000 | AFC Totton | 1 | 0 | Bemerton Heath H |
| 15/01/2000 | Andover (R) | 7 | 3 | Hamble Aerostructure |
| 15/01/2000 | BAT Sports | 0 | 0 | Gosport Borough |
| 15/01/2000 | Bournemouth (-2) | 1 | 0 | Cowes Sports |
| 15/01/2000 | Downton | 5 | 1 | Brockenhurst |
| 15/01/2000 | Eastleigh | 0 | 2 | Thatcham Town |
| 15/01/2000 | Lymington & New Milt | 2 | 1 | AFC Newbury |
| 15/01/2000 | Moneyfields | 1 | 2 | Wimborne Town |
| 08/01/2000 | AFC Newbury | 0 | 0 | Moneyfields |
| 08/01/2000 | Bournemouth (-2) | 0 | 2 | BAT Sports |
| 08/01/2000 | Cowes Sports | 7 | 2 | Portsmouth RN |
| 08/01/2000 | Hamble Aerostructure | 1 | 1 | Lymington & New Milt |
| 08/01/2000 | Whitchurch United | 2 | 1 | Downton |
| 03/01/2000 | AFC Totton | 7 | 1 | Bournemouth (-2) |
| 03/01/2000 | Andover (R) | 3 | 1 | Brockenhurst |
| 03/01/2000 | Cowes Sports | 1 | 1 | Whitchurch United |
| 03/01/2000 | Eastleigh | 2 | 0 | AFC Newbury |
| 03/01/2000 | Lymington & New Milt | 3 | 0 | Portsmouth RN |
| 03/01/2000 | Moneyfields | 1 | 1 | Hamble Aerostructure |
| 27/12/1999 | AFC Newbury | 1 | 0 | Thatcham Town |
| 27/12/1999 | BAT Sports | 0 | 2 | AFC Totton |
| 27/12/1999 | Bemerton Heath H | 7 | 4 | Downton |
| 27/12/1999 | Bournemouth (-2) | 1 | 5 | Christchurch |
| 27/12/1999 | East Cowes Victoria | 0 | 2 | Cowes Sports |
| 27/12/1999 | Gosport Borough | 0 | 0 | Fareham Town |
| 27/12/1999 | Hamble Aerostructure | 2 | 1 | Eastleigh |
| 18/12/1999 | Andover (R) | 7 | 1 | East Cowes Victoria |
| 18/12/1999 | Christchurch | 3 | 0 | BAT Sports |
| 18/12/1999 | Eastleigh | 2 | 1 | Portsmouth RN |
| 18/12/1999 | Fareham Town | 2 | 1 | Bournemouth (-2) |
| 18/12/1999 | Lymington & New Milt | 3 | 2 | Whitchurch United |
| 18/12/1999 | Thatcham Town | 2 | 0 | Hamble Aerostructure |
| 18/12/1999 | Wimborne Town | 5 | 1 | AFC Newbury |
| 11/12/1999 | Andover (R) | 1 | 1 | Bemerton Heath H |
| 11/12/1999 | Eastleigh | 3 | 0 | Brockenhurst |
| 11/12/1999 | Lymington & New Milt | 4 | 1 | East Cowes Victoria |
| 11/12/1999 | Moneyfields | 3 | 2 | Whitchurch United |
| 11/12/1999 | Thatcham Town | 4 | 2 | Portsmouth RN |
| 11/12/1999 | Wimborne Town | 5 | 1 | Hamble Aerostructure |
| 07/12/1999 | Hamble Aerostructure | 3 | 2 | AFC Newbury |
| 04/12/1999 | Bemerton Heath H | 2 | 1 | Christchurch |
| 04/12/1999 | Brockenhurst | 0 | 2 | Thatcham Town |
| 04/12/1999 | East Cowes Victoria | 3 | 4 | Moneyfields |
| 04/12/1999 | Gosport Borough | 0 | 3 | Andover (R) |
| 04/12/1999 | Portsmouth RN | 2 | 4 | Wimborne Town |
| 04/12/1999 | Whitchurch United | 0 | 1 | Eastleigh |
| 30/11/1999 | AFC Newbury | 1 | 3 | Whitchurch United |
| 30/11/1999 | Hamble Aerostructure | 1 | 3 | BAT Sports |
| 30/11/1999 | Lymington & New Milt | 4 | 1 | Downton |
| 27/11/1999 | AFC Newbury | 1 | 0 | Portsmouth RN |
| 27/11/1999 | Andover (R) | 8 | 0 | Bournemouth (-2) |
| 27/11/1999 | Cowes Sports | 1 | 2 | BAT Sports |
| 27/11/1999 | Downton | 0 | 7 | AFC Totton |
| 27/11/1999 | Eastleigh | 2 | 1 | East Cowes Victoria |
| 27/11/1999 | Fareham Town | 1 | 4 | Christchurch |
| 27/11/1999 | Moneyfields | 3 | 2 | Bemerton Heath H |
| 27/11/1999 | Thatcham Town | 2 | 4 | Whitchurch United |
| 27/11/1999 | Wimborne Town | 6 | 0 | Brockenhurst |
| 20/11/1999 | AFC Totton | 1 | 2 | Cowes Sports |
| 20/11/1999 | BAT Sports | 1 | 2 | Andover (R) |
| 20/11/1999 | Bemerton Heath H | 0 | 2 | Eastleigh |
| 20/11/1999 | Bournemouth (-2) | 0 | 6 | Lymington & New Milt |
| 20/11/1999 | Brockenhurst | 1 | 2 | AFC Newbury |
| 20/11/1999 | Christchurch | 2 | 2 | Downton |
| 20/11/1999 | East Cowes Victoria | 1 | 0 | Thatcham Town |
| 20/11/1999 | Gosport Borough | 1 | 2 | Moneyfields |
| 20/11/1999 | Portsmouth RN | 0 | 2 | Hamble Aerostructure |
| 20/11/1999 | Whitchurch United | 0 | 4 | Wimborne Town |
| 13/11/1999 | Downton | 1 | 3 | Fareham Town |
| 13/11/1999 | Eastleigh | 1 | 1 | Gosport Borough |
| 13/11/1999 | Hamble Aerostructure | 0 | 1 | Brockenhurst |
| 12/11/1999 | Moneyfields | 1 | 1 | Bournemouth (-2) |
| 12/11/1999 | Wimborne Town | 6 | 0 | East Cowes Victoria |
| 10/11/1999 | Fareham Town | 1 | 2 | Wimborne Town |
| 10/11/1999 | Moneyfields | 2 | 2 | AFC Newbury |
| 09/11/1999 | BAT Sports | 2 | 2 | Portsmouth RN |
| 09/11/1999 | Bournemouth (-2) | 1 | 4 | Eastleigh |
| 09/11/1999 | Gosport Borough | 2 | 0 | Thatcham Town |
| 09/11/1999 | Whitchurch United | 4 | 4 | Hamble Aerostructure |
| 06/11/1999 | BAT Sports | 2 | 2 | Moneyfields |
| 06/11/1999 | Bemerton Heath H | 4 | 4 | Wimborne Town |
| 06/11/1999 | East Cowes Victoria | 1 | 2 | AFC Newbury |
| 06/11/1999 | Thatcham Town | 1 | 4 | Cowes Sports |
| 02/11/1999 | AFC Newbury | 1 | 2 | Fareham Town |
| 02/11/1999 | AFC Totton | 2 | 0 | Hamble Aerostructure |
| 02/11/1999 | Brockenhurst | 4 | 1 | Portsmouth RN |
| 30/10/1999 | AFC Newbury | 1 | 1 | Bemerton Heath H |
| 30/10/1999 | Andover (R) | 4 | 1 | Fareham Town |
| 30/10/1999 | Cowes Sports | 6 | 1 | Downton |
| 30/10/1999 | Eastleigh | 1 | 1 | BAT Sports |
| 30/10/1999 | Hamble Aerostructure | 5 | 1 | East Cowes Victoria |
| 30/10/1999 | Lymington & New Milt | 2 | 1 | Christchurch |
| 30/10/1999 | Moneyfields | 0 | 3 | AFC Totton |
| 30/10/1999 | Portsmouth RN | 0 | 2 | Whitchurch United |
| 30/10/1999 | Thatcham Town | 3 | 1 | Bournemouth (-2) |
| 30/10/1999 | Wimborne Town | 4 | 1 | Gosport Borough |
| 26/10/1999 | Thatcham Town | 2 | 2 | Lymington & New Milt |
| 26/10/1999 | Wimborne Town | 3 | 2 | Andover (R) |
| 23/10/1999 | Bemerton Heath H | 2 | 0 | Hamble Aerostructure |
| 23/10/1999 | Downton | 2 | 5 | Andover (R) |
| 23/10/1999 | East Cowes Victoria | 1 | 2 | Portsmouth RN |
| 23/10/1999 | Moneyfields | 0 | 4 | Lymington & New Milt |
| 23/10/1999 | Whitchurch United | 1 | 1 | Brockenhurst |
| 16/10/1999 | AFC Newbury | 4 | 0 | Bournemouth (-2) |
| 16/10/1999 | Andover (R) | 5 | 0 | Cowes Sports |
| 16/10/1999 | Brockenhurst | 3 | 3 | East Cowes Victoria |
| 16/10/1999 | Eastleigh | 2 | 2 | Christchurch |
| 16/10/1999 | Hamble Aerostructure | 0 | 0 | Gosport Borough |
| 16/10/1999 | Moneyfields | 2 | 3 | Fareham Town |
| 16/10/1999 | Portsmouth RN | 4 | 4 | Bemerton Heath H |
| 16/10/1999 | Thatcham Town | 1 | 4 | AFC Totton |
| 16/10/1999 | Wimborne Town | 1 | 2 | BAT Sports |
| 09/10/1999 | AFC Totton | 0 | 2 | Wimborne Town |
| 09/10/1999 | BAT Sports | 2 | 1 | AFC Newbury |
| 09/10/1999 | Bemerton Heath H | 1 | 0 | Brockenhurst |
| 09/10/1999 | Bournemouth (-2) | 1 | 0 | Hamble Aerostructure |
| 09/10/1999 | Christchurch | 1 | 2 | Thatcham Town |
| 09/10/1999 | Cowes Sports | 0 | 1 | Lymington & New Milt |
| 09/10/1999 | Downton | 3 | 4 | Moneyfields |
| 09/10/1999 | East Cowes Victoria | 1 | 2 | Whitchurch United |
| 09/10/1999 | Fareham Town | 1 | 1 | Eastleigh |
| 09/10/1999 | Gosport Borough | 0 | 1 | Portsmouth RN |
| 05/10/1999 | Christchurch | 3 | 2 | Bemerton Heath H |
| 02/10/1999 | AFC Newbury | 1 | 0 | AFC Totton |
| 02/10/1999 | Brockenhurst | 1 | 1 | Gosport Borough |
| 02/10/1999 | Cowes Sports | 1 | 0 | Bemerton Heath H |
| 02/10/1999 | Eastleigh | 2 | 3 | Downton |
| 02/10/1999 | Thatcham Town | 5 | 3 | Fareham Town |
| 02/10/1999 | Wimborne Town | 2 | 0 | Christchurch |
| 29/09/1999 | Moneyfields | 3 | 0 | Cowes Sports |
| 28/09/1999 | Andover (R) | 0 | 0 | AFC Totton |
| 28/09/1999 | BAT Sports | 2 | 1 | Whitchurch United |
| 28/09/1999 | Brockenhurst | 0 | 2 | Christchurch |
| 28/09/1999 | Gosport Borough | 2 | 2 | AFC Newbury |
| 28/09/1999 | Lymington & New Milt | 4 | 1 | Eastleigh |
| 28/09/1999 | Thatcham Town | 1 | 2 | Bemerton Heath H |
| 28/09/1999 | Wimborne Town | 5 | 2 | Downton |
| 27/09/1999 | Portsmouth RN | 5 | 2 | Bournemouth (-2) |
| 25/09/1999 | Downton | 1 | 2 | Thatcham Town |
| 25/09/1999 | Lymington & New Milt | 9 | 0 | Gosport Borough |
| 22/09/1999 | Cowes Sports | 3 | 3 | Eastleigh |
| 21/09/1999 | BAT Sports | 2 | 1 | Thatcham Town |
| 21/09/1999 | Bemerton Heath H | 3 | 0 | East Cowes Victoria |
| 21/09/1999 | Bournemouth (-2) | 3 | 4 | Brockenhurst |
| 21/09/1999 | Gosport Borough | 4 | 0 | Whitchurch United |
| 21/09/1999 | Hamble Aerostructure | 1 | 4 | Christchurch |
| 20/09/1999 | Portsmouth RN | 0 | 4 | Fareham Town |
| 18/09/1999 | Brockenhurst | 0 | 4 | BAT Sports |
| 18/09/1999 | East Cowes Victoria | 0 | 0 | Gosport Borough |
| 18/09/1999 | Eastleigh | 1 | 3 | Andover (R) |
| 18/09/1999 | Fareham Town | 5 | 2 | Hamble Aerostructure |
| 18/09/1999 | Portsmouth RN | 0 | 2 | AFC Totton |
| 18/09/1999 | Whitchurch United | 0 | 1 | Bournemouth (-2) |
| 15/09/1999 | Cowes Sports | 2 | 1 | Wimborne Town |
| 14/09/1999 | AFC Totton | 0 | 2 | Brockenhurst |
| 14/09/1999 | Christchurch | 2 | 1 | Portsmouth RN |
| 14/09/1999 | Downton | 1 | 4 | AFC Newbury |
| 14/09/1999 | Eastleigh | 2 | 3 | Moneyfields |
| 14/09/1999 | Gosport Borough | 0 | 1 | Bemerton Heath H |
| 14/09/1999 | Lymington & New Milt | 0 | 0 | BAT Sports |
| 11/09/1999 | Andover (R) | 4 | 2 | Thatcham Town |
| 11/09/1999 | Bournemouth (-2) | 8 | 2 | East Cowes Victoria |
| 11/09/1999 | Christchurch | 1 | 2 | AFC Newbury |
| 11/09/1999 | Whitchurch United | 2 | 4 | Cowes Sports |
| 07/09/1999 | AFC Newbury | 3 | 1 | Eastleigh |
| 07/09/1999 | Bemerton Heath H | 1 | 0 | Fareham Town |
| 07/09/1999 | Bournemouth (-2) | 0 | 3 | AFC Totton |
| 07/09/1999 | Brockenhurst | 1 | 3 | Andover (R) |
| 07/09/1999 | East Cowes Victoria | 2 | 0 | Downton |
| 07/09/1999 | Gosport Borough | 0 | 4 | Christchurch |
| 07/09/1999 | Wimborne Town | 3 | 0 | Thatcham Town |
| 06/09/1999 | Portsmouth RN | 0 | 4 | Lymington & New Milt |
| 04/09/1999 | Andover (R) | 8 | 0 | Moneyfields |
| 04/09/1999 | Bemerton Heath H | 3 | 1 | Bournemouth (-2) |
| 04/09/1999 | East Cowes Victoria | 1 | 0 | BAT Sports |
| 04/09/1999 | Hamble Aerostructure | 0 | 2 | Downton |
| 04/09/1999 | Whitchurch United | 1 | 4 | AFC Totton |
| 31/08/1999 | Christchurch | 2 | 0 | Whitchurch United |
| 30/08/1999 | AFC Totton | 9 | 0 | East Cowes Victoria |
| 30/08/1999 | Andover (R) | 2 | 2 | AFC Newbury |
| 30/08/1999 | BAT Sports | 4 | 0 | Bemerton Heath H |
| 30/08/1999 | Bournemouth (-2) | 3 | 3 | Gosport Borough |
| 30/08/1999 | Cowes Sports | 3 | 1 | Hamble Aerostructure |
| 30/08/1999 | Downton | 4 | 1 | Portsmouth RN |
| 30/08/1999 | Fareham Town | 4 | 1 | Brockenhurst |
| 30/08/1999 | Lymington & New Milt | 1 | 2 | Wimborne Town |
| 30/08/1999 | Moneyfields | 1 | 0 | Thatcham Town |
| 28/08/1999 | AFC Newbury | 0 | 1 | Lymington & New Milt |
| 28/08/1999 | Bemerton Heath H | 2 | 2 | AFC Totton |
| 28/08/1999 | Brockenhurst | 2 | 0 | Downton |
| 28/08/1999 | East Cowes Victoria | 1 | 4 | Christchurch |
| 28/08/1999 | Gosport Borough | 0 | 3 | BAT Sports |
| 28/08/1999 | Hamble Aerostructure | 0 | 8 | Andover (R) |
| 28/08/1999 | Portsmouth RN | 1 | 4 | Cowes Sports |
| 28/08/1999 | Thatcham Town | 0 | 2 | Eastleigh |
| 28/08/1999 | Whitchurch United | 1 | 6 | Fareham Town |
| 28/08/1999 | Wimborne Town | 2 | 3 | Moneyfields |
| 25/08/1999 | Cowes Sports | 2 | 1 | Brockenhurst |
| 25/08/1999 | Fareham Town | 1 | 1 | East Cowes Victoria |
| 24/08/1999 | AFC Totton | 4 | 0 | Gosport Borough |
| 24/08/1999 | Andover (R) | 12 | 0 | Portsmouth RN |
| 24/08/1999 | BAT Sports | 2 | 1 | Bournemouth (-2) |
| 24/08/1999 | Downton | 1 | 1 | Whitchurch United |
| 24/08/1999 | Eastleigh | 1 | 0 | Wimborne Town |
| 24/08/1999 | Lymington & New Milt | 2 | 0 | Hamble Aerostructure |
| 21/08/1999 | Hamble Aerostructure | 0 | 4 | Moneyfields |
| 18/08/1999 | Cowes Sports | 1 | 1 | Bournemouth (-2) |
| 18/08/1999 | Fareham Town | 0 | 1 | AFC Totton |
| 18/08/1999 | Moneyfields | 2 | 0 | East Cowes Victoria |
| 17/08/1999 | AFC Newbury | 2 | 0 | Hamble Aerostructure |
| 17/08/1999 | Andover (R) | 1 | 2 | Gosport Borough |
| 17/08/1999 | Downton | 1 | 2 | BAT Sports |
| 17/08/1999 | Eastleigh | 2 | 0 | Whitchurch United |
| 17/08/1999 | Lymington & New Milt | 2 | 1 | Bemerton Heath H |
| 17/08/1999 | Thatcham Town | 0 | 0 | Brockenhurst |
| 17/08/1999 | Wimborne Town | 6 | 0 | Portsmouth RN |
| 14/08/1999 | AFC Newbury | 0 | 4 | Wimborne Town |
| 14/08/1999 | Bemerton Heath H | 2 | 4 | Cowes Sports |
| 14/08/1999 | Bournemouth (-2) | 1 | 1 | Fareham Town |
| 14/08/1999 | Brockenhurst | 2 | 1 | Moneyfields |
| 14/08/1999 | East Cowes Victoria | 5 | 2 | Andover (R) |
| 14/08/1999 | Gosport Borough | 0 | 2 | Downton |
| 14/08/1999 | Hamble Aerostructure | 0 | 3 | Thatcham Town |
| 14/08/1999 | Portsmouth RN | 1 | 1 | Eastleigh |
| 14/08/1999 | Whitchurch United | 0 | 2 | Lymington & New Milt |
| 13/08/1999 | BAT Sports | 2 | 2 | Christchurch |