| Time | Status | Match | FT | H1 | Stats | |
| 02/08/2009 15:00 |
(FT) | East Stirlingshire St Mirren |
3 6 |
3 4 |
MF | ME | |
| 01/08/2009 15:00 |
(FT) | Brechin City Elgin City |
4 0 |
1 0 |
MF | ME | |
| 01/08/2009 15:00 |
(FT) | Airdrie United Alloa Athletic |
0 0 |
0 0 |
MF | ME | |
| 90 minute[0-0],120 minute[0-0],Penalty Kick[3-4] | ||||||
| 01/08/2009 15:00 |
(FT) | Clyde Forfar Athletic |
1 3 |
1 0 |
MF | ME | |
| 01/08/2009 15:00 |
(FT) | Albion Rovers Livingston |
3 0 |
1 0 |
MF | ME | |
| 01/08/2009 15:00 |
(FT) | Peterhead Arbroath |
0 3 |
0 1 |
MF | ME | |
| 01/08/2009 15:00 |
(FT) | Cowdenbeath Greenock Morton |
1 3 |
1 2 |
MF | ME | |
| 01/08/2009 15:00 |
(FT) | Stirling Albion Ayr Utd |
1 1 |
1 0 |
MF | ME | |
| 90 minute[1-1],120 minute[1-2] | ||||||
| 01/08/2009 15:00 |
(FT) | Dundee Stranraer |
5 0 |
3 0 |
MF | ME | |
| 01/08/2009 15:00 |
(FT) | East Fife Raith Rovers |
2 3 |
2 0 |
MF | ME | |
| 01/08/2009 15:00 |
(FT) | Partick Thistle Berwick Rangers |
5 1 |
1 0 |
MF | ME | |
| 01/08/2009 15:00 |
(FT) | Ross County Montrose |
5 0 |
1 0 |
MF | ME | |
| 01/08/2009 15:00 |
(FT) | Stenhousemuir St Johnstone |
0 5 |
0 2 |
MF | ME | |
| 01/08/2009 15:00 |
(FT) | Dumbarton Dunfermline |
0 5 |
0 3 |
MF | ME | |
| 01/08/2009 15:00 |
(FT) | Inverness C.T. Annan Athletic |
4 0 |
1 0 |
MF | ME | |
| 01/08/2009 15:00 |
(FT) | Queens Park Queen of South |
1 4 |
0 3 |
MF | ME | |