| L | 2025-04-21 | Gillingham v AFC Wimbledon | 1–0 | League Two |
| W | 2024-12-30 | AFC Wimbledon v Gillingham | 1–0 | League Two |
| W | 2024-03-12 | AFC Wimbledon v Gillingham | 2–0 | League Two |
| L | 2023-11-28 | Gillingham v AFC Wimbledon | 1–0 | League Two |
| L | 2023-02-25 | Gillingham v AFC Wimbledon | 2–1 | League Two |
| W | 2022-07-30 | AFC Wimbledon v Gillingham | 2–0 | League Two |
| D | 2022-02-22 | Gillingham v AFC Wimbledon | 0–0 | League One |
| D | 2021-08-17 | AFC Wimbledon v Gillingham | 1–1 | League One |
| W | 2021-02-23 | AFC Wimbledon v Gillingham | 1–0 | League One |
| L | 2020-11-24 | Gillingham v AFC Wimbledon | 2–1 | League One |
| W | 2020-02-29 | Gillingham v AFC Wimbledon | 1–2 | League One |
| W | 2019-11-23 | AFC Wimbledon v Gillingham | 1–0 | League One |
| L | 2019-03-23 | AFC Wimbledon v Gillingham | 2–4 | League One |
| W | 2018-09-08 | Gillingham v AFC Wimbledon | 0–1 | League One |
| D | 2017-12-30 | Gillingham v AFC Wimbledon | 2–2 | League One |
| D | 2017-09-12 | AFC Wimbledon v Gillingham | 1–1 | League One |
| D | 2017-02-21 | Gillingham v AFC Wimbledon | 2–2 | League One |
| W | 2016-10-01 | AFC Wimbledon v Gillingham | 2–0 | League One |
| D | 2013-04-20 | Gillingham v AFC Wimbledon | 2–2 | League Two |
| L | 2012-10-27 | AFC Wimbledon v Gillingham | 0–1 | League Two |
| W | 2012-01-21 | Gillingham v AFC Wimbledon | 3–4 | League Two |
| W | 2011-10-01 | AFC Wimbledon v Gillingham | 3–1 | League Two |