4:0
Annan Athletic
Annan Athletic
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4:0
Annan Athletic
0:5
Greenock Morton
3:3
Annan Athletic
0:1
Dumbarton
Annan Athletic
1:0
Annan Athletic
4:0
Berwick Rangers
1:0
Hamilton
1:6
Ayr United
0:0
Annan Athletic
0:2
Kilmarnock
2:1
Annan Athletic
0:2
Annan Athletic
1:3
Motherwell
2:0
Annan Athletic
1:2
Stranraer
3:4
Queen of the South
5:1
Annan Athletic
3:0
Annan Athletic
2:0
Annan Athletic
1:2
Dunfermline Athletic
0:1
Partick Thistle
4:0
Annan Athletic
1:1
Annan Athletic
Championships
Championship 8391Scottish League Cup 2008/09, First RoundScottish League Cup 2009/10, First RoundScottish League Cup 2010/11, Second RoundScottish League Cup 2011/12, Third RoundScottish League Cup 2012/13, First RoundScottish League Cup 2013/14, Second RoundScottish League Cup 2014/15, First RoundScottish League Cup 2015/16, Third RoundScottish League Cup 2016/17, Second RoundScottish League Cup 2017/18, Group BScottish League Cup 2018/19, quarter-finals
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