| Essex Senior League | ||||
| Date | Home | H | A | Away |
| 06/05/2000 | Bowers United | 3 | 2 | Stansted |
| 06/05/2000 | Hullbridge Sports | 0 | 2 | East Ham United |
| 06/05/2000 | Woodford Town (P) | 1 | 7 | Southend Manor |
| 04/05/2000 | Eton Manor (-4) | 0 | 5 | Saffron Waldon Town |
| 04/05/2000 | Hullbridge Sports | 0 | 1 | Bowers United |
| 04/05/2000 | Stansted | 1 | 2 | Woodford Town (P) |
| 03/05/2000 | Bowers United | 0 | 0 | Sawbridgeworth Town |
| 02/05/2000 | Basildon United (-2) | 2 | 1 | Woodford Town (P) |
| 02/05/2000 | Eton Manor (-4) | 6 | 1 | Hullbridge Sports |
| 29/04/2000 | Basildon United (-2) | 1 | 4 | Burnham Ramblers |
| 29/04/2000 | Bowers United | 1 | 0 | Ilford |
| 29/04/2000 | Brentwood | 1 | 0 | Hullbridge Sports |
| 29/04/2000 | East Ham United | 0 | 0 | Sawbridgeworth Town |
| 29/04/2000 | Eton Manor (-4) | 1 | 3 | Concord Rangers |
| 29/04/2000 | Leyton (P) | 5 | 2 | Stansted |
| 29/04/2000 | Southend Manor | 3 | 3 | Saffron Waldon Town |
| 27/04/2000 | Hullbridge Sports | 2 | 3 | Leyton (P) |
| 25/04/2000 | Woodford Town (P) | 0 | 1 | Brentwood |
| 24/04/2000 | Basildon United (-2) | 1 | 5 | Bowers United |
| 24/04/2000 | Burnham Ramblers | 0 | 3 | Southend Manor |
| 24/04/2000 | Concord Rangers | 1 | 2 | Hullbridge Sports |
| 24/04/2000 | Ilford | 5 | 1 | Leyton (P) |
| 24/04/2000 | Sawbridgeworth Town | 3 | 1 | Stansted |
| 22/04/2000 | Stansted | 1 | 3 | Burnham Ramblers |
| 20/04/2000 | Basildon United (-2) | 0 | 1 | Brentwood |
| 20/04/2000 | Burnham Ramblers | 3 | 1 | Leyton (P) |
| 19/04/2000 | Eton Manor (-4) | 1 | 3 | Ilford |
| 18/04/2000 | Brentwood | 1 | 1 | Sawbridgeworth Town |
| 18/04/2000 | Burnham Ramblers | 1 | 1 | Concord Rangers |
| 18/04/2000 | Leyton (P) | 0 | 5 | Southend Manor |
| 18/04/2000 | Stansted | 1 | 5 | Saffron Waldon Town |
| 11/04/2000 | Burnham Ramblers | 1 | 0 | Stansted |
| 11/04/2000 | Saffron Waldon Town | 1 | 3 | Leyton (P) |
| 11/04/2000 | Sawbridgeworth Town | 10 | 0 | Woodford Town (P) |
| 10/04/2000 | Ilford | 4 | 1 | East Ham United |
| 08/04/2000 | Concord Rangers | 3 | 0 | Woodford Town (P) |
| 08/04/2000 | Eton Manor (-4) | 3 | 0 | Brentwood |
| 08/04/2000 | Hullbridge Sports | 0 | 2 | Saffron Waldon Town |
| 08/04/2000 | Leyton (P) | 2 | 1 | Bowers United |
| 08/04/2000 | Southend Manor | 4 | 3 | Sawbridgeworth Town |
| 08/04/2000 | Stansted | 0 | 4 | Ilford |
| 06/04/2000 | Hullbridge Sports | 8 | 0 | Woodford Town (P) |
| 05/04/2000 | Eton Manor (-4) | 0 | 0 | Leyton (P) |
| 01/04/2000 | Bowers United | 0 | 1 | Brentwood |
| 01/04/2000 | Hullbridge Sports | 2 | 3 | Eton Manor (-4) |
| 01/04/2000 | Southend Manor | 4 | 0 | Ilford |
| 28/03/2000 | Burnham Ramblers | 5 | 0 | Basildon United (-2) |
| 28/03/2000 | Sawbridgeworth Town | 2 | 1 | Leyton (P) |
| 25/03/2000 | Ilford | 3 | 2 | Eton Manor (-4) |
| 25/03/2000 | Stansted | 3 | 6 | Southend Manor |
| 23/03/2000 | Woodford Town (P) | 3 | 4 | Leyton (P) |
| 21/03/2000 | Basildon United (-2) | 3 | 3 | East Ham United |
| 21/03/2000 | Stansted | 1 | 1 | Eton Manor (-4) |
| 20/03/2000 | Ilford | 0 | 2 | Burnham Ramblers |
| 18/03/2000 | Bowers United | 0 | 0 | Basildon United (-2) |
| 18/03/2000 | Brentwood | 3 | 0 | East Ham United |
| 18/03/2000 | Burnham Ramblers | 3 | 0 | Woodford Town (P) |
| 18/03/2000 | Saffron Waldon Town | 8 | 0 | Hullbridge Sports |
| 18/03/2000 | Stansted | 2 | 2 | Concord Rangers |
| 14/03/2000 | Stansted | 0 | 3 | Hullbridge Sports |
| 14/03/2000 | Woodford Town (P) | 2 | 4 | East Ham United |
| 11/03/2000 | East Ham United | 1 | 0 | Stansted |
| 11/03/2000 | Hullbridge Sports | 3 | 2 | Basildon United (-2) |
| 11/03/2000 | Ilford | 3 | 0 | Concord Rangers |
| 11/03/2000 | Woodford Town (P) | 0 | 3 | Bowers United |
| 08/03/2000 | Bowers United | 1 | 2 | Burnham Ramblers |
| 08/03/2000 | Eton Manor (-4) | 0 | 1 | Basildon United (-2) |
| 07/03/2000 | Southend Manor | 1 | 0 | Woodford Town (P) |
| 04/03/2000 | Bowers United | 1 | 1 | Concord Rangers |
| 04/03/2000 | Burnham Ramblers | 5 | 1 | Eton Manor (-4) |
| 04/03/2000 | Leyton (P) | 0 | 1 | Brentwood |
| 04/03/2000 | Saffron Waldon Town | 8 | 0 | East Ham United |
| 26/02/2000 | Basildon United (-2) | 1 | 2 | Saffron Waldon Town |
| 26/02/2000 | Bowers United | 0 | 2 | Hullbridge Sports |
| 26/02/2000 | Brentwood | 2 | 1 | Southend Manor |
| 26/02/2000 | Concord Rangers | 0 | 2 | Sawbridgeworth Town |
| 26/02/2000 | Eton Manor (-4) | 1 | 0 | Stansted |
| 26/02/2000 | Leyton (P) | 5 | 0 | East Ham United |
| 26/02/2000 | Woodford Town (P) | 3 | 5 | Ilford |
| 22/02/2000 | East Ham United | 0 | 2 | Bowers United |
| 19/02/2000 | Ilford | 3 | 0 | Sawbridgeworth Town |
| 19/02/2000 | Saffron Waldon Town | 1 | 2 | Brentwood |
| 19/02/2000 | Southend Manor | 2 | 0 | Eton Manor (-4) |
| 19/02/2000 | Woodford Town (P) | 1 | 1 | Basildon United (-2) |
| 12/02/2000 | Concord Rangers | 2 | 1 | Basildon United (-2) |
| 05/02/2000 | Bowers United | 0 | 4 | Saffron Waldon Town |
| 05/02/2000 | Brentwood | 1 | 2 | Concord Rangers |
| 05/02/2000 | East Ham United | 0 | 3 | Southend Manor |
| 05/02/2000 | Stansted | 0 | 3 | Leyton (P) |
| 29/01/2000 | Basildon United (-2) | 4 | 0 | Stansted |
| 29/01/2000 | Ilford | 1 | 2 | Saffron Waldon Town |
| 29/01/2000 | Sawbridgeworth Town | 0 | 1 | Burnham Ramblers |
| 29/01/2000 | Southend Manor | 4 | 0 | Hullbridge Sports |
| 22/01/2000 | Concord Rangers | 1 | 1 | East Ham United |
| 15/01/2000 | Bowers United | 4 | 1 | Eton Manor (-4) |
| 15/01/2000 | Brentwood | 1 | 3 | Ilford |
| 15/01/2000 | Burnham Ramblers | 3 | 3 | East Ham United |
| 15/01/2000 | Hullbridge Sports | 0 | 3 | Sawbridgeworth Town |
| 15/01/2000 | Leyton (P) | 1 | 2 | Concord Rangers |
| 15/01/2000 | Saffron Waldon Town | 4 | 3 | Woodford Town (P) |
| 15/01/2000 | Southend Manor | 2 | 0 | Stansted |
| 08/01/2000 | Basildon United (-2) | 0 | 3 | Southend Manor |
| 08/01/2000 | Burnham Ramblers | 5 | 2 | Brentwood |
| 08/01/2000 | Concord Rangers | 1 | 4 | Ilford |
| 08/01/2000 | East Ham United | 2 | 3 | Hullbridge Sports |
| 08/01/2000 | Saffron Waldon Town | 2 | 1 | Bowers United |
| 08/01/2000 | Sawbridgeworth Town | 6 | 2 | Eton Manor (-4) |
| 03/01/2000 | Basildon United (-2) | 2 | 2 | Leyton (P) |
| 03/01/2000 | Eton Manor (-4) | 0 | 1 | East Ham United |
| 03/01/2000 | Ilford | 1 | 2 | Bowers United |
| 03/01/2000 | Sawbridgeworth Town | 2 | 2 | Saffron Waldon Town |
| 03/01/2000 | Southend Manor | 2 | 4 | Burnham Ramblers |
| 27/12/1999 | Brentwood | 4 | 1 | Eton Manor (-4) |
| 27/12/1999 | Burnham Ramblers | 2 | 1 | Hullbridge Sports |
| 27/12/1999 | Concord Rangers | 2 | 3 | Southend Manor |
| 27/12/1999 | East Ham United | 2 | 4 | Woodford Town (P) |
| 27/12/1999 | Leyton (P) | 0 | 3 | Ilford |
| 27/12/1999 | Stansted | 4 | 7 | Sawbridgeworth Town |
| 18/12/1999 | Ilford | 1 | 1 | Basildon United (-2) |
| 18/12/1999 | Saffron Waldon Town | 1 | 1 | Stansted |
| 18/12/1999 | Southend Manor | 3 | 1 | East Ham United |
| 18/12/1999 | Woodford Town (P) | 1 | 3 | Concord Rangers |
| 14/12/1999 | Leyton (P) | 2 | 1 | Saffron Waldon Town |
| 11/12/1999 | Basildon United (-2) | 1 | 5 | Concord Rangers |
| 11/12/1999 | Burnham Ramblers | 0 | 1 | Ilford |
| 11/12/1999 | East Ham United | 0 | 2 | Brentwood |
| 11/12/1999 | Southend Manor | 1 | 1 | Bowers United |
| 04/12/1999 | Basildon United (-2) | 1 | 2 | Hullbridge Sports |
| 04/12/1999 | Ilford | 3 | 0 | Southend Manor |
| 04/12/1999 | Saffron Waldon Town | 4 | 1 | Concord Rangers |
| 04/12/1999 | Sawbridgeworth Town | 3 | 4 | East Ham United |
| 04/12/1999 | Stansted | 1 | 3 | Brentwood |
| 04/12/1999 | Woodford Town (P) | 1 | 3 | Burnham Ramblers |
| 27/11/1999 | Saffron Waldon Town | 1 | 0 | Burnham Ramblers |
| 20/11/1999 | Brentwood | 1 | 2 | Bowers United |
| 20/11/1999 | East Ham United | 0 | 0 | Ilford |
| 20/11/1999 | Eton Manor (-4) | 3 | 3 | Burnham Ramblers |
| 20/11/1999 | Hullbridge Sports | 4 | 1 | Stansted |
| 20/11/1999 | Saffron Waldon Town | 3 | 2 | Basildon United (-2) |
| 20/11/1999 | Sawbridgeworth Town | 5 | 1 | Concord Rangers |
| 13/11/1999 | Concord Rangers | 2 | 0 | Brentwood |
| 13/11/1999 | East Ham United | 0 | 3 | Saffron Waldon Town |
| 13/11/1999 | Hullbridge Sports | 0 | 4 | Southend Manor |
| 12/11/1999 | Basildon United (-2) | 1 | 2 | Sawbridgeworth Town |
| 12/11/1999 | Leyton (P) | 0 | 1 | Woodford Town (P) |
| 06/11/1999 | Brentwood | 1 | 4 | Burnham Ramblers |
| 06/11/1999 | East Ham United | 0 | 0 | Basildon United (-2) |
| 06/11/1999 | Eton Manor (-4) | 1 | 3 | Woodford Town (P) |
| 06/11/1999 | Leyton (P) | 4 | 2 | Hullbridge Sports |
| 06/11/1999 | Saffron Waldon Town | 1 | 0 | Southend Manor |
| 06/11/1999 | Sawbridgeworth Town | 1 | 1 | Ilford |
| 06/11/1999 | Stansted | 1 | 5 | Bowers United |
| 23/10/1999 | Concord Rangers | 1 | 1 | Bowers United |
| 23/10/1999 | Eton Manor (-4) | 3 | 3 | Sawbridgeworth Town |
| 23/10/1999 | Hullbridge Sports | 1 | 2 | Brentwood |
| 23/10/1999 | Southend Manor | 5 | 1 | Leyton (P) |
| 23/10/1999 | Stansted | 4 | 2 | East Ham United |
| 23/10/1999 | Woodford Town (P) | 1 | 8 | Saffron Waldon Town |
| 16/10/1999 | Basildon United (-2) | 2 | 1 | Eton Manor (-4) |
| 16/10/1999 | Bowers United | 3 | 1 | East Ham United |
| 16/10/1999 | Brentwood | 4 | 3 | Woodford Town (P) |
| 16/10/1999 | Concord Rangers | 3 | 0 | Stansted |
| 16/10/1999 | Leyton (P) | 2 | 3 | Burnham Ramblers |
| 16/10/1999 | Saffron Waldon Town | 4 | 1 | Ilford |
| 16/10/1999 | Sawbridgeworth Town | 1 | 1 | Southend Manor |
| 12/10/1999 | Woodford Town (P) | 3 | 4 | Eton Manor (-4) |
| 09/10/1999 | Brentwood | 1 | 0 | Leyton (P) |
| 09/10/1999 | Burnham Ramblers | 1 | 3 | Saffron Waldon Town |
| 09/10/1999 | East Ham United | 0 | 0 | Concord Rangers |
| 09/10/1999 | Eton Manor (-4) | 2 | 2 | Bowers United |
| 09/10/1999 | Hullbridge Sports | 1 | 2 | Ilford |
| 09/10/1999 | Stansted | 2 | 3 | Basildon United (-2) |
| 09/10/1999 | Woodford Town (P) | 1 | 1 | Sawbridgeworth Town |
| 02/10/1999 | Concord Rangers | 1 | 1 | Burnham Ramblers |
| 02/10/1999 | Ilford | 6 | 1 | Woodford Town (P) |
| 02/10/1999 | Leyton (P) | 1 | 2 | Basildon United (-2) |
| 02/10/1999 | Saffron Waldon Town | 3 | 1 | Eton Manor (-4) |
| 02/10/1999 | Sawbridgeworth Town | 3 | 4 | Bowers United |
| 02/10/1999 | Southend Manor | 1 | 1 | Brentwood |
| 25/09/1999 | Bowers United | 1 | 0 | Leyton (P) |
| 11/09/1999 | Sawbridgeworth Town | 2 | 0 | Basildon United (-2) |
| 04/09/1999 | Concord Rangers | 1 | 1 | Eton Manor (-4) |
| 04/09/1999 | East Ham United | 0 | 2 | Burnham Ramblers |
| 04/09/1999 | Ilford | 2 | 2 | Hullbridge Sports |
| 30/08/1999 | Brentwood | 2 | 1 | Basildon United (-2) |
| 30/08/1999 | Hullbridge Sports | 1 | 1 | Burnham Ramblers |
| 30/08/1999 | Leyton (P) | 2 | 2 | Sawbridgeworth Town |
| 30/08/1999 | Southend Manor | 3 | 2 | Concord Rangers |
| 30/08/1999 | Woodford Town (P) | 5 | 3 | Stansted |
| 28/08/1999 | Bowers United | 2 | 7 | Southend Manor |
| 28/08/1999 | Brentwood | 4 | 2 | Saffron Waldon Town |
| 28/08/1999 | Burnham Ramblers | 3 | 0 | Sawbridgeworth Town |
| 28/08/1999 | Concord Rangers | 3 | 0 | Leyton (P) |
| 28/08/1999 | East Ham United | 0 | 2 | Eton Manor (-4) |
| 28/08/1999 | Ilford | 3 | 1 | Stansted |
| 28/08/1999 | Woodford Town (P) | 3 | 3 | Hullbridge Sports |
| 21/08/1999 | Sawbridgeworth Town | 0 | 6 | Brentwood |
| 17/08/1999 | Burnham Ramblers | 3 | 1 | Bowers United |
| 17/08/1999 | Hullbridge Sports | 0 | 1 | Concord Rangers |
| 17/08/1999 | Leyton (P) | 0 | 0 | Eton Manor (-4) |
| 17/08/1999 | Saffron Waldon Town | 1 | 1 | Sawbridgeworth Town |
| 17/08/1999 | Southend Manor | 3 | 2 | Basildon United (-2) |
| 16/08/1999 | Ilford | 3 | 0 | Brentwood |
| 14/08/1999 | Basildon United (-2) | 2 | 5 | Ilford |
| 14/08/1999 | Bowers United | 4 | 3 | Woodford Town (P) |
| 14/08/1999 | Brentwood | 1 | 3 | Stansted |
| 14/08/1999 | Concord Rangers | 1 | 1 | Saffron Waldon Town |
| 14/08/1999 | East Ham United | 2 | 2 | Leyton (P) |
| 14/08/1999 | Eton Manor (-4) | 0 | 0 | Southend Manor |
| 14/08/1999 | Sawbridgeworth Town | 2 | 1 | Hullbridge Sports |