| Date | Home | Time/Results | Away | League | Season | Venue | Article |
|---|---|---|---|---|---|---|---|
Leyton Pennant  | 4 - 1 |  Brentwood Town | Essex Thameside Trophy | 1999-2000 | Recap | ||
| Brentwood Town | 1 - 1 | Leyton Pennant | Eastern Floodlit Cup | 1999-2000 | Recap | ||
| Leyton Pennant | 0 - 1 | Brentwood Town | Eastern Floodlit Cup | 1999-2000 | Recap | ||
| Brentwood Town | 1 - 0 | Leyton Pennant | Essex Thameside Trophy | 2002-3 | Recap | ||
Waltham Forest  | 3 - 4 | Brentwood Town | Isthmian League Division 1 North | 2007-8 | Wadham Lodge | Recap | |
| Brentwood Town | 4 - 0 | Waltham Forest | Isthmian League Division 1 North | 2007-8 | Recap | ||
| Waltham Forest | 1 - 2 | Brentwood Town | Friendly | 2016-17 | Recap | ||
Walthamstow  | 0 - 1 | Brentwood Town | Essex Senior Cup | 2021-22 | Wadham Lodge | Recap | |
| Walthamstow | 1 - 2 | Brentwood Town | Isthmian League Division 1 North | 2023-24 | Wadham Lodge | Recap | |
| Brentwood Town | 2 - 0 | Walthamstow | Isthmian League Division 1 North | 2023-24 | Recap | ||
| Brentwood Town | 3 - 2 | Walthamstow | Isthmian League Division 1 North | 2024-25 | Recap | ||
| Walthamstow | 2 - 0 | Brentwood Town | Isthmian League Division 1 North | 2024-25 | Wadham Lodge | Recap | |
| Walthamstow | 1 - 2 | Brentwood Town | Friendly | 2025-26 | Wadham Lodge | Recap |
