The Gray Trophy 2008-2009
(Presented by RS and CRW Gray)
1st Round
| 1 | Dundee University | 3 - 2 | Kelso AFC |
| 2 | Dundee Shamrock | 1 - 3 | Arbroath Amateurs |
| 3 | NCR AFC | 4 - 0 | Letham Lads Club |
| 4 | Harris Academy FP | 0 - 6 | Broughty United |
| 5 | Arbroath HSFP | 5 - 2 | Douglas Sports Club |
| 6 | Bank Street Athletic | w/o - scr | Logie Harp |
2nd Round
| 1 | Broughty United | 2 - 0 | Arbroath Amateurs |
| 2 | Newport AFC | 4 - 2 | Arbroath HSFP |
| 3 | Dundee University | 2 - 1 | Merpro AFC |
| 4 | NCR AFC | 1 - 3 | Bank Street Athletic |
Semi Finals
| 1 | Dundee University | 2 - 1 | Newport AFC |
| 2 | Bank Street Athletic | 2 - 1 | Broughty United |
FINAL
| Dundee University | 1 - 2 | Bank Street Athletic |
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