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| Date | Match | Score |
|---|---|---|
| 10.07.2021 | Airdrie United - Annan Athletic | 1 : 1 |
| 24.07.2018 | Airdrie United - Annan Athletic | 4 : 1 |
| Date | Match | Score | Res |
|---|---|---|---|
| 08.09.2026 | Airdrie United - St. Mirren U21 | 1 - 0 | W |
| 05.09.2026 | Queen of the South - Airdrie United | 2 - 1 | L |
| 29.08.2026 | Airdrie United - East Fife | 0 - 0 | D |
| 25.08.2026 | Airdrie United - Stirling Albion | 1 - 3 | L |
| 22.08.2026 | Airdrie United - Ross County | 1 - 3 | L |
| Date | Match | Score | Res |
|---|---|---|---|
| 08.09.2026 | Annan Athletic - Motherwell U21 | 4 - 0 | W |
| 05.09.2026 | Kelty Hearts - Annan Athletic | 2 - 1 | L |
| 29.08.2026 | Annan Athletic - Dumbarton | 2 - 0 | W |
| 25.08.2026 | Annan Athletic - Berwick Rangers | 2 - 2 | D |
| 22.08.2026 | Edinburgh City - Annan Athletic | 1 - 0 | L |