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Ryman League
Premier Division
Season 1999-2000
| Saturday 14th August 1999 |
| Aylesbury United | 1-0 | Walton & Hersham |
| Billericay Town | 1-0 | Hampton & Richmond |
| Carshalton Athletic | 2-2 | Enfield |
| Dulwich Hamlet | 1-2 | Boreham Wood |
| Farnborough Town | 3-0 | Basingstoke Town |
| Gravesend & Northfleet | 0-1 | Canvey Island |
| Harrow Borough | 1-1 | Dagenham & Redbridge |
| Hendon | 1-2 | Aldershot Town |
| Heybridge Swifts | 2-3 | Hitchin Town |
| Purfleet | 0-0 | Chesham United |
| St Albans City | 0-1 | Slough Town |
| Tuesday 17th August 1999 |
| Aldershot Town | 2-1 | Gravesend & Northfleet |
| Basingstoke Town | 4-2 | Aylesbury United |
| Boreham Wood | 1-1 | Farnborough Town |
| Canvey Island | 2-0 | Harrow Borough |
| Chesham United | 3-4 | St Albans City |
| Dagenham & Redbridge | 3-1 | Carshalton Athletic |
| Enfield | 3-2 | Heybridge Swifts |
| Hampton & Richmond | 1-1 | Purfleet |
| Hitchin Town | 4-0 | Billericay Town |
| Slough Town | 1-1 | Hendon |
| Walton & Hersham | 0-3 | Dulwich Hamlet |
| Saturday 21st August 1999 |
| Aldershot Town | 0-1 | Billericay Town |
| Basingstoke Town | 2-2 | Heybridge Swifts |
| Boreham Wood | 0-2 | Carshalton Athletic |
| Canvey Island | 0-1 | St Albans City |
| Chesham United | 1-1 | Gravesend & Northfleet |
| Dagenham & Redbridge | 4-1 | Aylesbury United |
| Enfield | 3-2 | Dulwich Hamlet |
| Hampton & Richmond | 1-0 | Farnborough Town |
| Hitchin Town | 1-0 | Hendon |
| Slough Town | 3-0 | Purfleet |
| Walton & Hersham | 3-1 | Harrow Borough |
| Monday 23rd August 1999 |
| Carshalton Athletic | 1-1 | Slough Town |
| Dulwich Hamlet | 3-2 | Basingstoke Town |
| Hendon | 3-2 | Canvey Island |
| Purfleet | 2-4 | Aldershot Town |
| St Albans City | 2-1 | Hitchin Town |
| Tuesday 24th August 1999 |
| Aylesbury United | 0-1 | Boreham Wood |
| Billericay Town | 2-1 | Chesham United |
| Farnborough Town | 2-1 | Dagenham & Redbridge |
| Gravesend & Northfleet | 0-0 | Hampton & Richmond |
| Harrow Borough | 1-2 | Enfield |
| Heybridge Swifts | 5-1 | Walton & Hersham |
| Saturday 28th August 1999 |
| Aylesbury United | 3-3 | Canvey Island |
| Billericay Town | 1-0 | Boreham Wood |
| Carshalton Athletic | 2-0 | Hitchin Town |
| Dulwich Hamlet | 2-0 | Hampton & Richmond |
| Farnborough Town | 1-1 | Enfield |
| Gravesend & Northfleet | 1-0 | Slough Town |
| Harrow Borough | 0-2 | Chesham United |
| Hendon | 0-1 | Dagenham & Redbridge |
| Heybridge Swifts | 1-3 | Aldershot Town |
| Purfleet | 1-2 | Basingstoke Town |
| St Albans City | 1-1 | Walton & Hersham |
| Monday 30th August 1999 |
| Aldershot Town | 0-2 | St Albans City |
| Basingstoke Town | 2-0 | Carshalton Athletic |
| Boreham Wood | 0-1 | Harrow Borough |
| Canvey Island | 2-0 | Purfleet |
| Chesham United | 1-2 | Dulwich Hamlet |
| Dagenham & Redbridge | 2-0 | Heybridge Swifts |
| Enfield | 3-1 | Aylesbury United |
| Hampton & Richmond | 1-2 | Hendon |
| Hitchin Town | 1-0 | Gravesend & Northfleet |
| Slough Town | 4-0 | Billericay Town |
| Walton & Hersham | 0-0 | Farnborough Town |
| Friday 3rd September 1999 |
| Dagenham & Redbridge | 2-1 | Billericay Town |
| Saturday 4th September 1999 |
| Basingstoke Town | 0-2 | St Albans City |
| Boreham Wood | 1-1 | Purfleet |
| Canvey Island | 1-0 | Carshalton Athletic |
| Chesham United | 1-1 | Heybridge Swifts |
| Enfield | 5-3 | Hendon |
| Gravesend & Northfleet | 1-1 | Walton & Hersham |
| Hampton & Richmond | 2-1 | Aylesbury United |
| Hitchin Town | 1-1 | Farnborough Town |
| Slough Town | 2-1 | Dulwich Hamlet |
| Sunday 5th September 1999 |
| Aldershot Town | 1-2 | Harrow Borough |
| Monday 6th September 1999 |
| Carshalton Athletic | 0-2 | Walton & Hersham |
| Dulwich Hamlet | 0-0 | Dagenham & Redbridge |
| Hendon | 4-2 | Chesham United |
| Purfleet | 3-0 | Hitchin Town |
| St Albans City | 1-1 | Hampton & Richmond |
| Tuesday 7th September 1999 |
| Aylesbury United | 3-0 | Aldershot Town |
| Billericay Town | 0-0 | Canvey Island |
| Farnborough Town | 0-1 | Slough Town |
| Gravesend & Northfleet | 1-2 | Enfield |
| Harrow Borough | 1-1 | Basingstoke Town |
| Heybridge Swifts | 0-1 | Boreham Wood |
| Saturday 11th September 1999 |
| Billericay Town | 3-3 | Gravesend & Northfleet |
| Boreham Wood | 0-1 | Dagenham & Redbridge |
| Chesham United | 2-0 | Aldershot Town |
| Dulwich Hamlet | 2-0 | Harrow Borough |
| Enfield | 2-0 | Basingstoke Town |
| Farnborough Town | 3-1 | Aylesbury United |
| Heybridge Swifts | 0-2 | Carshalton Athletic |
| Hitchin Town | 2-2 | Hampton & Richmond |
| St Albans City | 3-0 | Hendon |
| Slough Town | 1-2 | Canvey Island |
| Walton & Hersham | 0-3 | Purfleet |
| Saturday 25th September 1999 |
| Aldershot Town | 5-1 | Hitchin Town |
| Aylesbury United | 2-2 | Heybridge Swifts |
| Basingstoke Town | 1-3 | Walton & Hersham |
| Canvey Island | 2-1 | Chesham United |
| Carshalton Athletic | 0-5 | Dulwich Hamlet |
| Dagenham & Redbridge | 4-0 | Enfield |
| Gravesend & Northfleet | 1-2 | St Albans City |
| Hampton & Richmond | 1-1 | Slough Town |
| Harrow Borough | 1-3 | Farnborough Town |
| Hendon | 2-1 | Boreham Wood |
| Purfleet | 2-2 | Billericay Town |
| Saturday 2nd October 1999 |
| Boreham Wood | 0-4 | Hampton & Richmond |
| Chesham United | 2-1 | Walton & Hersham |
| Tuesday 5th October 1999 |
| Walton & Hersham | 2-2 | Slough Town |
| Saturday 9th October 1999 |
| Billericay Town | 3-5 | Dulwich Hamlet |
| Enfield | 4-1 | Walton & Hersham |
| Farnborough Town | 1-2 | Canvey Island |
| Saturday 16th October 1999 |
| Aylesbury United | 3-2 | Carshalton Athletic |
| Basingstoke Town | 1-1 | Boreham Wood |
| Hampton & Richmond | 0-1 | Chesham United |
| Harrow Borough | 2-0 | Heybridge Swifts |
| Purfleet | 0-0 | Gravesend & Northfleet |
| Tuesday 19th October 1999 |
| Farnborough Town | 1-1 | Purfleet |
| Hitchin Town | 4-3 | Aylesbury United |
| Saturday 23rd October 1999 |
| Aylesbury United | 2-3 | Dulwich Hamlet |
| Billericay Town | 3-1 | St Albans City |
| Boreham Wood | 1-0 | Enfield |
| Canvey Island | 0-3 | Hitchin Town |
| Carshalton Athletic | 3-1 | Harrow Borough |
| Chesham United | 3-0 | Slough Town |
| Dagenham & Redbridge | 2-0 | Walton & Hersham |
| Gravesend & Northfleet | 1-0 | Basingstoke Town |
| Heybridge Swifts | 1-2 | Farnborough Town |
| Purfleet | 4-1 | Hendon |
| Saturday 30th October 1999 |
| Basingstoke Town | 0-4 | Dagenham & Redbridge |
| Dulwich Hamlet | 2-1 | Heybridge Swifts |
| Farnborough Town | 4-1 | Carshalton Athletic |
| Gravesend & Northfleet | 2-2 | Billericay Town |
| Hampton & Richmond | 0-2 | Canvey Island |
| Harrow Borough | 4-1 | Aylesbury United |
| Hitchin Town | 0-2 | Chesham United |
| Walton & Hersham | 3-1 | Boreham Wood |
| Saturday 6th November 1999 |
| Aldershot Town | 1-0 | Boreham Wood |
| Billericay Town | 5-0 | Harrow Borough |
| Canvey Island | 1-0 | Enfield |
| Gravesend & Northfleet | 5-1 | Farnborough Town |
| Hampton & Richmond | 2-1 | Basingstoke Town |
| Hendon | 1-2 | Dulwich Hamlet |
| Hitchin Town | 0-2 | Dagenham & Redbridge |
| Purfleet | 1-0 | Heybridge Swifts |
| St Albans City | 4-0 | Carshalton Athletic |
| Slough Town | 1-2 | Aylesbury United |
| Tuesday 9th November 1999 |
| Chesham United | 1-0 | Enfield |
| Friday 12th November 1999 |
| Aylesbury United | 0-3 | Purfleet |
| Dagenham & Redbridge | 5-0 | Hampton & Richmond |
| Heybridge Swifts | 2-4 | Gravesend & Northfleet |
| Saturday 13th November 1999 |
| Boreham Wood | 1-3 | Slough Town |
| Carshalton Athletic | 3-3 | Billericay Town |
| Dulwich Hamlet | 2-0 | Canvey Island |
| Enfield | 1-4 | Aldershot Town |
| Harrow Borough | 0-2 | St Albans City |
| Walton & Hersham | 4-3 | Hitchin Town |
| Sunday 14th November 1999 |
| Basingstoke Town | 0-1 | Chesham United |
| Farnborough Town | 0-1 | Hendon |
| Saturday 20th November 1999 |
| Billericay Town | 0-3 | Farnborough Town |
| Canvey Island | 1-1 | Walton & Hersham |
| Chesham United | 5-0 | Boreham Wood |
| Gravesend & Northfleet | 5-0 | Aylesbury United |
| Hampton & Richmond | 1-4 | Heybridge Swifts |
| Hitchin Town | 2-0 | Basingstoke Town |
| Purfleet | 1-1 | Harrow Borough |
| St Albans City | 4-1 | Dulwich Hamlet |
| Slough Town | 2-3 | Dagenham & Redbridge |
| Saturday 27th November 1999 |
| Boreham Wood | 2-3 | St Albans City |
| Dagenham & Redbridge | 1-1 | Chesham United |
| Monday 29th November 1999 |
| Carshalton Athletic | 1-2 | Gravesend & Northfleet |
| Tuesday 30th November 1999 |
| Aylesbury United | 0-1 | Billericay Town |
| Dagenham & Redbridge | 3-1 | Aldershot Town |
| Walton & Hersham | 1-2 | Hendon |
| Saturday 4th December 1999 |
| Aylesbury United | 2-2 | Hampton & Richmond |
| Basingstoke Town | 2-2 | Purfleet |
| Boreham Wood | 0-2 | Billericay Town |
| Carshalton Athletic | 3-1 | Canvey Island |
| Dagenham & Redbridge | 4-0 | Hendon |
| Dulwich Hamlet | 2-3 | Slough Town |
| Enfield | 0-1 | Gravesend & Northfleet |
| Farnborough Town | 1-1 | Hitchin Town |
| Harrow Borough | 0-1 | Aldershot Town |
| Heybridge Swifts | 2-1 | Chesham United |
| Walton & Hersham | 1-1 | St Albans City |
| Saturday 11th December 1999 |
| Aldershot Town | 3-2 | Dulwich Hamlet |
| Billericay Town | 0-3 | Walton & Hersham |
| Canvey Island | 6-1 | Heybridge Swifts |
| Chesham United | 2-1 | Farnborough Town |
| Gravesend & Northfleet | 3-0 | Boreham Wood |
| Hendon | 4-3 | Basingstoke Town |
| St Albans City | 1-1 | Aylesbury United |
| Tuesday 14th December 1999 |
| Gravesend & Northfleet | 4-1 | Harrow Borough |
| Hampton & Richmond | 2-1 | Enfield |
| Saturday 18th December 1999 |
| Aylesbury United | 2-3 | Hendon |
| Basingstoke Town | 2-0 | Billericay Town |
| Boreham Wood | 2-5 | Aldershot Town |
| Carshalton Athletic | 0-1 | St Albans City |
| Dagenham & Redbridge | 4-1 | Hitchin Town |
| Dulwich Hamlet | 3-2 | Purfleet |
| Enfield | 1-1 | Canvey Island |
| Farnborough Town | 3-2 | Gravesend & Northfleet |
| Harrow Borough | 0-1 | Slough Town |
| Heybridge Swifts | 2-2 | Hampton & Richmond |
| Walton & Hersham | 1-2 | Chesham United |
| Monday 27th December 1999 |
| Aldershot Town | 1-0 | Farnborough Town |
| Billericay Town | 1-2 | Heybridge Swifts |
| Canvey Island | 3-1 | Dagenham & Redbridge |
| Chesham United | 1-1 | Aylesbury United |
| Gravesend & Northfleet | 3-1 | Dulwich Hamlet |
| Hitchin Town | 1-3 | Boreham Wood |
| Purfleet | 1-1 | Carshalton Athletic |
| St Albans City | 5-0 | Enfield |
| Slough Town | 1-4 | Basingstoke Town |
| Wednesday 29th December 1999 |
| Hampton & Richmond | 0-2 | Walton & Hersham |
| Monday 3rd January 2000 |
| Aylesbury United | 2-2 | Slough Town |
| Basingstoke Town | 2-0 | Hampton & Richmond |
| Boreham Wood | 3-2 | Canvey Island |
| Dagenham & Redbridge | 2-1 | Gravesend & Northfleet |
| Dulwich Hamlet | 1-0 | Hendon |
| Enfield | 1-1 | Hitchin Town |
| Farnborough Town | 1-0 | St Albans City |
| Harrow Borough | 1-1 | Billericay Town |
| Heybridge Swifts | 0-0 | Purfleet |
| Walton & Hersham | 0-1 | Aldershot Town |
| Saturday 8th January 2000 |
| Aldershot Town | 0-1 | Heybridge Swifts |
| Billericay Town | 0-4 | Dagenham & Redbridge |
| Canvey Island | 2-3 | Aylesbury United |
| Chesham United | 1-2 | Harrow Borough |
| Hendon | 2-2 | Enfield |
| Hitchin Town | 3-2 | Carshalton Athletic |
| Purfleet | 3-2 | Boreham Wood |
| St Albans City | 4-1 | Basingstoke Town |
| Slough Town | 1-2 | Farnborough Town |
| Walton & Hersham | 2-2 | Gravesend & Northfleet |
| Monday 10th January 2000 |
| Carshalton Athletic | 0-3 | Chesham United |
| Tuesday 11th January 2000 |
| Basingstoke Town | 2-1 | Aldershot Town |
| Saturday 15th January 2000 |
| Aylesbury United | 0-2 | Dagenham & Redbridge |
| Dulwich Hamlet | 0-0 | Enfield |
| Harrow Borough | 3-0 | Hampton & Richmond |
| Slough Town | 3-0 | Hitchin Town |
| Tuesday 18th January 2000 |
| Heybridge Swifts | 2-1 | St Albans City |
| Saturday 22nd January 2000 |
| Aldershot Town | 2-1 | Hendon |
| Basingstoke Town | 2-2 | Farnborough Town |
| Boreham Wood | 0-0 | Dulwich Hamlet |
| Canvey Island | 4-1 | Gravesend & Northfleet |
| Chesham United | 1-0 | Purfleet |
| Dagenham & Redbridge | 4-1 | Harrow Borough |
| Enfield | 3-2 | Carshalton Athletic |
| Hitchin Town | 1-2 | Heybridge Swifts |
| Slough Town | 0-3 | St Albans City |
| Walton & Hersham | 0-3 | Aylesbury United |
| Monday 24th January 2000 |
| St Albans City | 1-3 | Dagenham & Redbridge |
| Saturday 29th January 2000 |
| Aylesbury United | 3-0 | Basingstoke Town |
| Billericay Town | 1-1 | Hitchin Town |
| Carshalton Athletic | 1-1 | Dagenham & Redbridge |
| Dulwich Hamlet | 1-0 | Walton & Hersham |
| Farnborough Town | 0-2 | Boreham Wood |
| Gravesend & Northfleet | 1-1 | Aldershot Town |
| Harrow Borough | 1-3 | Canvey Island |
| Hendon | 1-1 | Slough Town |
| Heybridge Swifts | 2-1 | Enfield |
| Purfleet | 0-0 | Hampton & Richmond |
| St Albans City | 1-1 | Chesham United |
| Friday 4th February 2000 |
| Purfleet | 2-0 | Dagenham & Redbridge |
| Saturday 5th February 2000 |
| Basingstoke Town | 2-0 | Dulwich Hamlet |
| Boreham Wood | 2-2 | Aylesbury United |
| Canvey Island | 0-0 | Hendon |
| Enfield | 0-3 | Harrow Borough |
| Hampton & Richmond | 1-0 | Gravesend & Northfleet |
| Hitchin Town | 2-2 | St Albans City |
| Slough Town | 2-1 | Carshalton Athletic |
| Monday 7th February 2000 |
| Hendon | 2-0 | Gravesend & Northfleet |
| St Albans City | 2-4 | Purfleet |
| Tuesday 8th February 2000 |
| Aldershot Town | 4-0 | Carshalton Athletic |
| Canvey Island | 3-1 | Basingstoke Town |
| Saturday 12th February 2000 |
| Aylesbury United | 1-0 | Enfield |
| Billericay Town | 3-1 | Slough Town |
| Carshalton Athletic | 3-3 | Basingstoke Town |
| Dulwich Hamlet | 1-2 | Chesham United |
| Gravesend & Northfleet | 1-1 | Hitchin Town |
| Harrow Borough | 1-3 | Boreham Wood |
| Heybridge Swifts | 5-4 | Dagenham & Redbridge |
| St Albans City | 0-1 | Aldershot Town |
| Monday 14th February 2000 |
| Carshalton Athletic | 3-0 | Boreham Wood |
| Tuesday 15th February 2000 |
| Farnborough Town | 0-1 | Hampton & Richmond |
| Saturday 19th February 2000 |
| Aldershot Town | 1-1 | Aylesbury United |
| Basingstoke Town | 2-0 | Harrow Borough |
| Boreham Wood | 0-0 | Heybridge Swifts |
| Canvey Island | 3-0 | Billericay Town |
| Chesham United | 2-1 | Hendon |
| Dagenham & Redbridge | 3-0 | Dulwich Hamlet |
| Enfield | 3-0 | Farnborough Town |
| Hampton & Richmond | 2-2 | St Albans City |
| Hitchin Town | 1-0 | Purfleet |
| Slough Town | 2-1 | Gravesend & Northfleet |
| Walton & Hersham | 0-2 | Carshalton Athletic |
| Monday 21st February 2000 |
| Hendon | 2-0 | Heybridge Swifts |
| Tuesday 22nd February 2000 |
| Enfield | 1-2 | Purfleet |
| Gravesend & Northfleet | 3-2 | Chesham United |
| Saturday 26th February 2000 |
| Billericay Town | 1-1 | Hendon |
| Boreham Wood | 3-4 | Basingstoke Town |
| Canvey Island | 2-1 | Aldershot Town |
| Carshalton Athletic | 2-1 | Aylesbury United |
| Chesham United | 1-0 | Hampton & Richmond |
| Dagenham & Redbridge | 2-1 | St Albans City |
| Farnborough Town | 2-0 | Dulwich Hamlet |
| Gravesend & Northfleet | 1-2 | Purfleet |
| Hitchin Town | 1-2 | Slough Town |
| Walton & Hersham | 0-2 | Enfield |
| Saturday 4th March 2000 |
| Aldershot Town | 1-0 | Dagenham & Redbridge |
| Aylesbury United | 3-1 | Hitchin Town |
| Basingstoke Town | 0-1 | Canvey Island |
| Dulwich Hamlet | 1-2 | Billericay Town |
| Enfield | 2-2 | Chesham United |
| Hampton & Richmond | 1-1 | Boreham Wood |
| Harrow Borough | 6-0 | Gravesend & Northfleet |
| Purfleet | 4-0 | Farnborough Town |
| St Albans City | 2-0 | Heybridge Swifts |
| Slough Town | 3-1 | Walton & Hersham |
| Monday 6th March 2000 |
| Hendon | 1-1 | Hitchin Town |
| Tuesday 7th March 2000 |
| Hampton & Richmond | 3-0 | Dulwich Hamlet |
| Harrow Borough | 0-1 | Walton & Hersham |
| Saturday 11th March 2000 |
| Billericay Town | 1-1 | Purfleet |
| Boreham Wood | 0-2 | Hendon |
| Chesham United | 2-1 | Canvey Island |
| Dulwich Hamlet | 1-3 | Carshalton Athletic |
| Farnborough Town | 0-0 | Harrow Borough |
| Heybridge Swifts | 0-0 | Aylesbury United |
| Hitchin Town | 1-2 | Aldershot Town |
| St Albans City | 0-1 | Gravesend & Northfleet |
| Slough Town | 1-1 | Hampton & Richmond |
| Walton & Hersham | 1-0 | Basingstoke Town |
| Sunday 12th March 2000 |
| Enfield | 1-1 | Dagenham & Redbridge |
| Monday 13th March 2000 |
| Hendon | 0-1 | Harrow Borough |
| Walton & Hersham | 0-1 | Heybridge Swifts |
| Tuesday 14th March 2000 |
| Enfield | 1-1 | Billericay Town |
| Hampton & Richmond | 0-1 | Carshalton Athletic |
| Saturday 18th March 2000 |
| Aldershot Town | 4-1 | Chesham United |
| Aylesbury United | 1-2 | Farnborough Town |
| Basingstoke Town | 2-1 | Enfield |
| Canvey Island | 2-0 | Slough Town |
| Carshalton Athletic | 1-1 | Heybridge Swifts |
| Dagenham & Redbridge | 2-0 | Boreham Wood |
| Hampton & Richmond | 2-1 | Hitchin Town |
| Harrow Borough | 1-0 | Dulwich Hamlet |
| Hendon | 0-3 | St Albans City |
| Purfleet | 3-1 | Walton & Hersham |
| Monday 20th March 2000 |
| Hendon | 1-0 | Hampton & Richmond |
| St Albans City | 2-5 | Canvey Island |
| Tuesday 21st March 2000 |
| Farnborough Town | 1-2 | Walton & Hersham |
| Heybridge Swifts | 2-0 | Basingstoke Town |
| Hitchin Town | 4-0 | Harrow Borough |
| Slough Town | 2-1 | Enfield |
| Saturday 25th March 2000 |
| Aldershot Town | 2-0 | Slough Town |
| Aylesbury United | 3-1 | Harrow Borough |
| Billericay Town | 0-0 | Enfield |
| Boreham Wood | 1-0 | Walton & Hersham |
| Canvey Island | 1-2 | Hampton & Richmond |
| Carshalton Athletic | 1-1 | Farnborough Town |
| Chesham United | 2-1 | Hitchin Town |
| Dagenham & Redbridge | 1-0 | Basingstoke Town |
| Gravesend & Northfleet | 1-0 | Hendon |
| Heybridge Swifts | 1-1 | Dulwich Hamlet |
| Purfleet | 3-3 | St Albans City |
| Monday 27th March 2000 |
| Hendon | 3-2 | Billericay Town |
| Tuesday 28th March 2000 |
| Heybridge Swifts | 1-2 | Harrow Borough |
| Saturday 1st April 2000 |
| Basingstoke Town | 2-0 | Gravesend & Northfleet |
| Dulwich Hamlet | 3-0 | Aylesbury United |
| Enfield | 1-1 | Boreham Wood |
| Farnborough Town | 0-1 | Heybridge Swifts |
| Hampton & Richmond | 0-1 | Aldershot Town |
| Harrow Borough | 0-0 | Carshalton Athletic |
| Hendon | 1-3 | Purfleet |
| Hitchin Town | 3-3 | Canvey Island |
| St Albans City | 1-2 | Billericay Town |
| Slough Town | 2-0 | Chesham United |
| Walton & Hersham | 0-2 | Dagenham & Redbridge |
| Monday 3rd April 2000 |
| Purfleet | 2-0 | Canvey Island |
| Tuesday 4th April 2000 |
| Dagenham & Redbridge | 3-2 | Farnborough Town |
| Hampton & Richmond | 1-2 | Billericay Town |
| Saturday 8th April 2000 |
| Aldershot Town | 3-0 | Walton & Hersham |
| Billericay Town | 1-0 | Basingstoke Town |
| Canvey Island | 0-1 | Boreham Wood |
| Chesham United | 0-0 | Carshalton Athletic |
| Gravesend & Northfleet | 1-2 | Dagenham & Redbridge |
| Hendon | 1-0 | Aylesbury United |
| Hitchin Town | 2-1 | Enfield |
| Purfleet | 1-1 | Dulwich Hamlet |
| St Albans City | 0-0 | Farnborough Town |
| Slough Town | 2-3 | Harrow Borough |
| Monday 10th April 2000 |
| Carshalton Athletic | 0-1 | Hendon |
| Dulwich Hamlet | 1-2 | Hitchin Town |
| Purfleet | 2-0 | Slough Town |
| Tuesday 11th April 2000 |
| Aldershot Town | 3-1 | Canvey Island |
| Chesham United | 1-1 | Billericay Town |
| Saturday 15th April 2000 |
| Aylesbury United | 0-2 | St Albans City |
| Basingstoke Town | 1-1 | Hendon |
| Dagenham & Redbridge | 3-1 | Purfleet |
| Dulwich Hamlet | 1-2 | Aldershot Town |
| Enfield | 1-3 | Slough Town |
| Harrow Borough | 4-0 | Hitchin Town |
| Monday 17th April 2000 |
| Dulwich Hamlet | 1-3 | Farnborough Town |
| Tuesday 18th April 2000 |
| Billericay Town | 3-2 | Aldershot Town |
| Carshalton Athletic | 1-1 | Hampton & Richmond |
| Harrow Borough | 2-1 | Hendon |
| Heybridge Swifts | 1-1 | Slough Town |
| Friday 21st April 2000 |
| Canvey Island | 0-1 | Dulwich Hamlet |
| Saturday 22nd April 2000 |
| Aldershot Town | 0-4 | Enfield |
| Billericay Town | 2-0 | Carshalton Athletic |
| Chesham United | 1-1 | Basingstoke Town |
| Gravesend & Northfleet | 1-1 | Heybridge Swifts |
| Hampton & Richmond | 2-3 | Dagenham & Redbridge |
| Hendon | 5-3 | Farnborough Town |
| Hitchin Town | 0-2 | Walton & Hersham |
| Purfleet | 0-2 | Aylesbury United |
| St Albans City | 3-2 | Harrow Borough |
| Slough Town | 2-3 | Boreham Wood |
| Monday 24th April 2000 |
| Aylesbury United | 3-2 | Chesham United |
| Basingstoke Town | 1-0 | Slough Town |
| Boreham Wood | 0-0 | Hitchin Town |
| Carshalton Athletic | 0-0 | Purfleet |
| Dagenham & Redbridge | 2-0 | Canvey Island |
| Dulwich Hamlet | 1-5 | Gravesend & Northfleet |
| Farnborough Town | 0-0 | Aldershot Town |
| Heybridge Swifts | 1-2 | Billericay Town |
| Walton & Hersham | 1-3 | Hampton & Richmond |
| Wednesday 26th April 2000 |
| Aldershot Town | 1-1 | Hampton & Richmond |
| Boreham Wood | 3-4 | Gravesend & Northfleet |
| Farnborough Town | 0-1 | Chesham United |
| Friday 28th April 2000 |
| Purfleet | 4-2 | Enfield |
| Saturday 29th April 2000 |
| Aldershot Town | 5-2 | Basingstoke Town |
| Billericay Town | 5-0 | Aylesbury United |
| Canvey Island | 2-0 | Farnborough Town |
| Chesham United | 0-3 | Dagenham & Redbridge |
| Gravesend & Northfleet | 0-5 | Carshalton Athletic |
| Hampton & Richmond | 3-1 | Harrow Borough |
| Hendon | 2-2 | Walton & Hersham |
| Hitchin Town | 2-0 | Dulwich Hamlet |
| St Albans City | 0-0 | Boreham Wood |
| Slough Town | 2-1 | Heybridge Swifts |
| Monday 1st May 2000 |
| Hendon | 2-0 | Carshalton Athletic |
| Heybridge Swifts | 3-0 | Canvey Island |
| Walton & Hersham | 0-1 | Billericay Town |
| Tuesday 2nd May 2000 |
| Enfield | 4-0 | St Albans City |
| Slough Town | 0-0 | Aldershot Town |
| Thursday 4th May 2000 |
| Aldershot Town | 0-2 | Purfleet |
| Saturday 6th May 2000 |
| Aylesbury United | 4-1 | Gravesend & Northfleet |
| Basingstoke Town | 1-1 | Hitchin Town |
| Boreham Wood | 1-3 | Chesham United |
| Carshalton Athletic | 3-0 | Aldershot Town |
| Dagenham & Redbridge | 2-1 | Slough Town |
| Dulwich Hamlet | 3-2 | St Albans City |
| Enfield | 2-3 | Hampton & Richmond |
| Farnborough Town | 2-0 | Billericay Town |
| Harrow Borough | 2-3 | Purfleet |
| Heybridge Swifts | 1-2 | Hendon |
| Walton & Hersham | 0-3 | Canvey Island |
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