| Saturday 27th September 2008 | |||
| First Round | |||
| Banks O'Dee | 10-0 | Fort William | |
| Clachnacuddin | 4-0 | Burntisland Shipyard | |
| Dalbeattie Star | 5-1 | Lossiemouth | |
| Edinburgh City | 2-0 | Nairn County | |
| Edinburgh University | 1-2 | Civil Service Str | |
| Fraserburgh | 6-3 | Hawick Royal Albert | |
| Glasgow University | 0-1 | Vale of Leithen | |
| Golspie Sutherland | 0-3 | Threave Rovers | |
| Huntly | 1-0 | Girvan | |
| Inverurie Locos | 5-2 | Deveronvale | |
| Lochee United | 3-1 | Bathgate Thistle | |
| Newton Stewart Ath | 1-1 | Brora Rangers | |
| Pollok | 1-1 | Spartans | |
| Preston Athletic | 3-1 | Gala Fairydean | |
| Rothes | 1-4 | Buckie Thistle | |
| Selkirk | 1-1 | Coldstream | |
| St Cuthberts Wndrs | 0-3 | Wick Academy | |
| Wigtown and Bladnoch | 2-2 | Forres Mechanics | |
» Scottish FA Cup 2008-2009 : Results
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