| L | 2026-03-10 | Gillingham v Milton Keynes Dons | 1–5 | League Two |
| L | 2025-10-04 | Milton Keynes Dons v Gillingham | 3–2 | League Two |
| W | 2025-04-12 | Gillingham v Milton Keynes Dons | 1–0 | League Two |
| W | 2024-12-14 | Milton Keynes Dons v Gillingham | 0–1 | League Two |
| L | 2024-01-27 | Milton Keynes Dons v Gillingham | 2–1 | League Two |
| W | 2023-10-07 | Gillingham v Milton Keynes Dons | 2–1 | League Two |
| D | 2022-01-01 | Milton Keynes Dons v Gillingham | 0–0 | League One |
| L | 2021-09-18 | Gillingham v Milton Keynes Dons | 1–4 | League One |
| W | 2021-03-02 | Gillingham v Milton Keynes Dons | 3–2 | League One |
| L | 2020-10-17 | Milton Keynes Dons v Gillingham | 2–0 | League One |
| W | 2019-12-21 | Gillingham v Milton Keynes Dons | 3–1 | League One |
| L | 2018-03-29 | Gillingham v Milton Keynes Dons | 1–2 | League One |
| L | 2017-08-19 | Milton Keynes Dons v Gillingham | 1–0 | League One |
| L | 2017-04-01 | Milton Keynes Dons v Gillingham | 3–2 | League One |
| W | 2016-12-17 | Gillingham v Milton Keynes Dons | 1–0 | League One |
| W | 2015-02-14 | Gillingham v Milton Keynes Dons | 4–2 | League One |
| L | 2014-08-09 | Milton Keynes Dons v Gillingham | 4–2 | League One |
| W | 2014-03-25 | Milton Keynes Dons v Gillingham | 0–1 | League One |
| W | 2013-10-05 | Gillingham v Milton Keynes Dons | 3–2 | League One |
| D | 2010-03-27 | Gillingham v Milton Keynes Dons | 2–2 | League One |
| L | 2009-10-17 | Milton Keynes Dons v Gillingham | 2–0 | League One |
| W | 2006-04-01 | Milton Keynes Dons v Gillingham | 1–2 | League One |
| W | 2005-12-31 | Gillingham v Milton Keynes Dons | 3–0 | League One |