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August 2014
Sat 2 15:00 Dunfermline Athletic 5-1 Annan Athletic 2-0 1,544 Round 1 Report
August 2013
Sat 3 15:00 Queen of the South 3-0 Annan Athletic 0-0 1,588 Round 1 Report
August 2012
Sat 4 15:00 Hamilton Academical 2-0 Annan Athletic 0-0 620 Round 1 Report
July 2011
Sat 30 15:00 Annan Athletic 1-2 Dunfermline Athletic 1-1 767 Round 1 Report
July 2010
Sat 31 15:00 Annan Athletic 0-1 Partick Thistle 0-0 1,025 Round 1 Report
August 2009
Sat 1 15:00 Inverness Caledonian Thistle 4-0 Annan Athletic 1,095 Round 1 Report
August 2008
Tue 5 19:30 Dumbarton 1-1 Annan Athletic 462 Round 1 Report
After extra time