| 2022-08-06 15:00:42August 6, 2022 | Annan Athletic  | 2 - 1 |  Stenhousemuir | 15:00:423:00 pm | N/A |
| 2022-04-02 15:00:42April 2, 2022 | Stenhousemuir | 0 - 1 | Annan Athletic | 15:00:423:00 pm | N/A |
| 2022-02-05 15:00:52February 5, 2022 | Annan Athletic | 0 - 2 | Stenhousemuir | 15:00:523:00 pm | N/A |
| 2021-11-13 15:00:47November 13, 2021 | Stenhousemuir | 2 - 0 | Annan Athletic | 15:00:473:00 pm | N/A |
| 2021-09-11 15:00:22September 11, 2021 | Annan Athletic | 1 - 2 | Stenhousemuir | 15:00:223:00 pm | N/A |
| 2021-04-27 19:00:08April 27, 2021 | Annan Athletic | 1 - 1 | Stenhousemuir | 19:00:087:00 pm | N/A |
| 2021-04-20 19:45:13April 20, 2021 | Annan Athletic | 5 - 1 | Stenhousemuir | 19:45:137:45 pm | N/A |
| 2020-11-21 15:00:08November 21, 2020 | Stenhousemuir | 1 - 2 | Annan Athletic | 15:00:083:00 pm | N/A |
| 2020-04-25 15:00:41April 25, 2020 | Stenhousemuir | - | Annan Athletic | 15:00:41Postponed | N/A |
| 2020-02-01 15:00:05February 1, 2020 | Annan Athletic | 0 - 3 | Stenhousemuir | 15:00:053:00 pm | N/A |
| 2019-12-07 15:00:11December 7, 2019 | Stenhousemuir | 1 - 2 | Annan Athletic | 15:00:113:00 pm | N/A |
| 2019-08-31 15:00:19August 31, 2019 | Annan Athletic | 1 - 1 | Stenhousemuir | 15:00:193:00 pm | N/A |
| 2019-05-11 15:00:27May 11, 2019 | Stenhousemuir | 1 - 2 | Annan Athletic | 15:00:273:00 pm | N/A |
| 2019-05-07 19:45:43May 7, 2019 | Annan Athletic | 2 - 0 | Stenhousemuir | 19:45:437:45 pm | N/A |
| 2018-04-14 15:00:10April 14, 2018 | Stenhousemuir | 3 - 2 | Annan Athletic | 15:00:103:00 pm | N/A |
| 2018-02-24 15:00:35February 24, 2018 | Annan Athletic | 2 - 0 | Stenhousemuir | 15:00:353:00 pm | N/A |
| 2017-12-09 15:00:19December 9, 2017 | Stenhousemuir | 1 - 3 | Annan Athletic | 15:00:193:00 pm | N/A |
| 2017-09-16 15:00:55September 16, 2017 | Annan Athletic | 1 - 1 | Stenhousemuir | 15:00:553:00 pm | N/A |
2 vs 2 
Annan Athletic
2 vs 2 
Annan Athletic
