- 27 January 2026, Inverness Caledonian Thistle FC vs Stenhousemuir FC, 1-0, Lose
- 13 January 2026, Stirling Albion FC vs Stenhousemuir FC, 1-2, Win
- 09 December 2025, Stenhousemuir FC vs Annan Athletic FC, 2-0, Win
- 19 November 2025, Dumbarton FC vs Stenhousemuir FC, 0-2, Win
- 11 October 2025, Stenhousemuir FC vs FC Motherwell B, 4-0, Win
- 09 December 2025, Stenhousemuir FC vs Annan Athletic FC, 2-0, Lose
- 11 November 2025, Annan Athletic FC vs FC Kilmarnock B, 6-0, Win
- 11 October 2025, Hamilton Academical FC vs Annan Athletic FC, 1-2, Win
- 23 September 2025, Annan Athletic FC vs Glasgow Rangers B, 4-3, Win
- 06 September 2025, Annan Athletic FC vs St Mirren FC B, 2-2, Draw
In this Challenge Cup encounter, Stenhousemuir FC secured a 2-0 victory over Annan Athletic FC, capitalizing effectively on their opportunities. The home team's ability to convert chances was crucial, with both goals coming at strategic moments in the match. The first goal, scored in the first half at the 34th minute, set the tone, while the second in the 52nd minute further solidified their lead. Both goals were a testament to Stenhousemuir’s clinical finishing and strategic timing.
Annan Athletic, while maintaining a slight advantage in corner kicks with six compared to Stenhousemuir’s five, struggled to translate set-piece opportunities into goals. Despite the equal number of fouls committed by both sides, Annan's discipline faltered with a red card incident, reducing them to ten players and significantly impacting their defensive solidity and attacking potential. This dismissal was a pivotal factor, hindering their chances of mounting a comeback after conceding the second goal.
Teamwork and coordination were evident in Stenhousemuir's performance, as they maintained discipline throughout, avoiding yellow and red cards entirely. Their ability to manage the game while remaining composed was key to their success. Annan, on the other hand, missed the opportunity to exploit their set pieces, and the lack of creativity in breaking Stenhousemuir’s defence was exacerbated by their ill-discipline, ultimately leading to their downfall in this contest.
Form Guide
| Lose | 1-0 | Inverness Caledonian Thistle FC vs Stenhousemuir FC | |
| Win | 1-2 | Stirling Albion FC vs Stenhousemuir FC | |
| Win | 2-0 | Stenhousemuir FC vs Annan Athletic FC | |
| Win | 0-2 | Dumbarton FC vs Stenhousemuir FC | |
| Win | 4-0 | Stenhousemuir FC vs FC Motherwell B |
- PLAYED
- 5
- WINS
- 4
- GOALS
- 10:2
- GOALS / MATCH
- 2
- Stenhousemuir FC has four wins in its last five matches with a goal difference of 10:2, scoring 2 goals average
| Lose | 2-0 | Stenhousemuir FC vs Annan Athletic FC | |
| Win | 6-0 | Annan Athletic FC vs FC Kilmarnock B | |
| Win | 1-2 | Hamilton Academical FC vs Annan Athletic FC | |
| Win | 4-3 | Annan Athletic FC vs Glasgow Rangers B | |
| Draw | 2-2 | Annan Athletic FC vs St Mirren FC B |
- PLAYED
- 5
- WINS
- 3
- GOALS
- 14:8
- GOALS / MATCH
- 2.8
- Annan Athletic FC has won three out of its last five matches with a goal difference of 14:8, scoring 2.8 goals average
Stenhousemuir FC H2H Annan Athletic FC
| Home game | Stenhousemuir FC | 2 | 0 | Annan Athletic FC | Away game | Challenge Cup | |
| Away game | Stenhousemuir FC | 3 | 1 | Annan Athletic FC | Home game | Challenge Cup | |
| Away game | Stenhousemuir FC | 2 | 0 | Annan Athletic FC | Home game | League One | |
| Home game | Stenhousemuir FC | 1 | 1 | Annan Athletic FC | Away game | League One | |
| Away game | Stenhousemuir FC | 1 | 1 | Annan Athletic FC | Home game | League One |
- PLAYED
- 5
- WINS
- 3
- GOALS
- 9:3
- GOALS / MATCH
- 1.80
- In the last five matches that these two sides meet, Stenhousemuir FC overtook Annan Athletic FC three times
- Stenhousemuir FC won three times and had two draw
- Teams played five times head-to-head in the current season with the goals score 9:3; average goals per match – 1.80
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