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versus
November 2013
Tue 12 19:30 Annan Athletic 2-4 Stenhousemuir 1-0 421 Round 3
After extra time (2-2 after 90 mins)
Sat 2 15:00 Stenhousemuir 2-2 Annan Athletic 0-1 309 Round 3
October 2013
Sat 19 15:00 Annan Athletic 4-0 Buckie Thistle 3-0 338 Round 2
Sat 5 15:00 Buckie Thistle 0-0 Annan Athletic 0-0 320 Round 2
October 2012
Sat 6 15:00 Annan Athletic 1-2 Buckie Thistle 0-0 404 Round 2 Report
September 2012
Sat 29 15:00 Buckie Thistle 0-0 Annan Athletic 0-0 356 Round 2 Report
November 2011
Sat 19 15:00 Stenhousemuir 4-0 Annan Athletic 4-0 602 Round 3 Report
October 2011
Sat 29 15:00 Annan Athletic 2-0 Alloa Athletic 1-0 502 Round 2 Report
Sat 22 15:00 Alloa Athletic 2-2 Annan Athletic 1-1 490 Round 2 Report
January 2011
Tue 4 19:30 Annan Athletic 2-5 Brechin City 1-4 512 Round 3 Report
December 2010
Tue 28 19:30 Annan Athletic P-P Brechin City Round 3 Report
Tue 21 19:30 Annan Athletic P-P Brechin City Round 3 Report
Wed 15 19:30 Annan Athletic P-P Brechin City Round 3 Report
Tue 7 19:30 Annan Athletic P-P Brechin City Round 3 Report
November 2010
Sat 27 15:00 Annan Athletic P-P Brechin City Round 3 Report
Sat 20 15:00 Brechin City 2-2 Annan Athletic 1-0 402 Round 3 Report
October 2010
Sat 30 15:00 Annan Athletic 5-0 Preston Ath 4-0 426 Round 2 Report
Sat 23 15:00 Preston Ath 0-0 Annan Athletic 0-0 350 Round 2 Report
October 2009
Sat 24 15:00 Cove Rangers 2-1 Annan Athletic 278 Round 2 Report
November 2008
Sat 1 15:00 Annan Athletic 1-2 Spartans 652 Round 2 Report
October 2008
Sat 25 15:00 Annan Athletic P-P Pollok/ Spartans Round 2 Report
Sat 25 15:00 Annan Athletic P-P Spartans Round 2 Report
October 2007
Sat 27 14:00 Annan Athletic 2-5 Huntly 243 Round 2 Report
December 2006
Sat 9 13:30 Annan Athletic 0-3 Greenock Morton 1,200 Round 2 Report
Sat 9 15:00 Annan Athletic P-P Greenock Round 2 Report