Saturday 31st October
Scottish League Two
- Stirling Albion 1 , Annan Athletic 0 at Full timeStirling AlbionAnnan AthleticFull time
Saturday 24th October
Scottish League Two
- Annan Athletic 1 , Stranraer 1 at Full timeAnnan AthleticStranraerFull time
Saturday 17th October
Scottish League Two
- Cowdenbeath 0 , Annan Athletic 3 at Full timeCowdenbeathAnnan AthleticFull time
Tuesday 13th October
League Cup - Group F
- Ayr United 1 , Annan Athletic 0 at Full timeAyr UnitedAnnan AthleticFull time
Saturday 10th October
League Cup - Group F
- Annan Athletic 1 , Stranraer 1 at Full time , Stranraer win 5 - 4 on penaltiesAnnan AthleticStranraerFull timeStranraer win 5 - 4 on penalties
Tuesday 6th October
League Cup - Group F
- Annan Athletic 3 , Hamilton Academical 1 at Full timeAnnan AthleticHamilton AcademicalFull time
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