- 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
- 26 August 2025, Annan Athletic FC vs Stenhousemuir FC, 1-3, Lose
- 12 August 2025, Kelty Hearts FC vs Annan Athletic FC, 1-0, Lose
- 11 October 2025, Stenhousemuir FC vs FC Motherwell B, 4-0, Win
- 23 September 2025, Stenhousemuir FC vs East Kilbride FC, 3-0, Win
- 06 September 2025, Stenhousemuir FC vs FC Kilmarnock B, 4-0, Win
- 26 August 2025, Annan Athletic FC vs Stenhousemuir FC, 1-3, Win
- 12 August 2025, Stenhousemuir FC vs Glasgow Rangers B, 2-1, Win
The match between Annan Athletic FC and Stenhousemuir FC in the Challenge Cup on 26 August 2025 ended with a decisive 3-1 victory for the away team, Stenhousemuir FC. The opening half saw an intense and aggressive play, with yellow cards flying by the 36th minute. Stenhousemuir seized the opportunity to control the game, opening the score in the first half. Their disciplined approach was evident, as they managed just one yellow card, contrasting with Annan Athletic's six.
Annan Athletic's aggressive approach significantly impacted the game flow. Their six yellow cards revealed a lack of discipline, contributing to a fragmented game plan. This was detrimental when Stenhousemuir's two second-half goals placed additional pressure on Annan. Despite having more corner opportunities (8 to Stenhousemuir's 6), Annan struggled to convert these into goal-scoring opportunities, evidencing a disconnect between their midfield and forward line.
Stenhousemuir's strategic use of their chances was crucial. They capitalized on key moments with goals at critical junctures, notably just after Annan's equalizer, which psychologically shifted the momentum back to Stenhousemuir. Their ability to convert three out of their opportunities effectively demonstrated superior finishing skills and coordination among their attackers. Overall, the match was a testament to Stenhousemuir's efficient execution and Annan Athletic's struggles with discipline and coordination.
Form Guide
| 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 | |
| Lose | 1-3 | Annan Athletic FC vs Stenhousemuir FC | |
| Lose | 1-0 | Kelty Hearts FC vs Annan Athletic FC |
- PLAYED
- 5
- WINS
- 2
- GOALS
- 9:10
- GOALS / MATCH
- 1.8
- Annan Athletic FC has two wins in its last five matches with a goal difference of 9:10, scoring 1.8 goals average
| Win | 4-0 | Stenhousemuir FC vs FC Motherwell B | |
| Win | 3-0 | Stenhousemuir FC vs East Kilbride FC | |
| Win | 4-0 | Stenhousemuir FC vs FC Kilmarnock B | |
| Win | 1-3 | Annan Athletic FC vs Stenhousemuir FC | |
| Win | 2-1 | Stenhousemuir FC vs Glasgow Rangers B |
- PLAYED
- 5
- WINS
- 5
- GOALS
- 16:2
- GOALS / MATCH
- 3.2
- Stenhousemuir FC has won five matches in a row with a goal difference of 16:2, scoring 3.2 goals average
Annan Athletic FC H2H Stenhousemuir FC
| Home game | Annan Athletic FC | 1 | 3 | Stenhousemuir FC | Away game | Challenge Cup | |
| Home game | Annan Athletic FC | 0 | 2 | Stenhousemuir FC | Away game | League One | |
| Away game | Annan Athletic FC | 1 | 1 | Stenhousemuir FC | Home game | League One | |
| Home game | Annan Athletic FC | 1 | 1 | Stenhousemuir FC | Away game | League One | |
| Away game | Annan Athletic FC | 1 | 5 | Stenhousemuir FC | Home game | League One |
- PLAYED
- 5
- WINS
- 0
- GOALS
- 4:12
- GOALS / MATCH
- 0.80
- Annan Athletic FC lost three times in head-to-head matches
- Teams played five times head-to-head in the current season with the goals score 4:12; average goals per match – 0.80
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