| Date | Match | Score | |
|---|---|---|---|
| W | 2023-04-01 | East Fife v Annan Athletic | 0–1 |
| W | 2023-01-28 | Annan Athletic v East Fife | 3–0 |
| W | 2022-12-03 | East Fife v Annan Athletic | 1–3 |
| D | 2022-09-17 | Annan Athletic v East Fife | 2–2 |
| L | 2016-03-12 | East Fife v Annan Athletic | 4–2 |
| L | 2016-01-16 | Annan Athletic v East Fife | 2–4 |
| W | 2015-10-31 | East Fife v Annan Athletic | 0–1 |
| W | 2015-09-05 | Annan Athletic v East Fife | 2–0 |
| W | 2015-04-18 | Annan Athletic v East Fife | 2–1 |
| L | 2015-02-28 | East Fife v Annan Athletic | 2–1 |
| W | 2014-12-13 | Annan Athletic v East Fife | 2–1 |
| D | 2014-10-18 | East Fife v Annan Athletic | 1–1 |
League meetings on record only — domestic cup and European ties are not yet in the archive, so this is the league ledger of the rivalry, not every match ever played. Results from PitchVAR's own football warehouse.