| 27 Sep 2008 |
Berwick Rangers
|
3–0
|
Annan Athletic
|
H
|
SCO · Scottish League Two
|
| 20 Sep 2008 |
Annan Athletic
|
1–3
|
Forfar Athletic
|
A
|
SCO · Scottish League Two
|
| 13 Sep 2008 |
Elgin City
|
1–2
|
Annan Athletic
|
A
|
SCO · Scottish League Two
|
| 30 Aug 2008 |
Annan Athletic
|
2–4
|
Albion Rovers
|
A
|
SCO · Scottish League Two
|
| 23 Aug 2008 |
Montrose
|
1–1
|
Annan Athletic
|
D
|
SCO · Scottish League Two
|
| 16 Aug 2008 |
Annan Athletic
|
2–1
|
East Stirlingshire
|
H
|
SCO · Scottish League Two
|
| 09 Aug 2008 |
Annan Athletic
|
1–1
|
Stenhousemuir
|
D
|
SCO · Scottish League Two
|
| 05 Aug 2008 |
Dumbarton
|
1–1
|
Annan Athletic
|
D
|
SCO · Scottish League Cup
|
| 02 Aug 2008 |
Cowdenbeath
|
1–4
|
Annan Athletic
|
A
|
SCO · Scottish League Two
|
| 27 Oct 2007 |
Annan Athletic
|
2–5
|
Huntly
|
A
|
SCO · Scottish Cup
|
| 09 Dec 2006 |
Annan Athletic
|
0–3
|
Greenock Morton
|
A
|
SCO · Scottish Cup
|
