Alliance Challenge Cup 2008
1st Round
| 1 | Arbroath HSFP | 1 - 3 | Dundee University |
| 2 | Barnhill AFC | 1- 4 | NCR AFC |
| 3 | Broughty United | 1 - 2 aet | Carnoustie YM 'A' |
| 4 | Carnoustie YM 'B' | 4 - 1 | Dee Club |
| 5 | Kelso AFC | 2 - 2 aet pens 4 - 2 | Harris Academy FP |
| 6 | Monifieth Tayside | scr - w/o | Arbroath Harp |
| 7 | Riverside Athletic | 0 - 2 | Invergowrie AFC |
2nd Round
| 1 | Arbroath Harp | 2 - 2 aet pens 1 - 3 | Dundee University |
| 2 | Carnoustie YM 'B' | 1 - 1 aet pens 3 - 4 | Carnoustie YM 'A' |
| 3 | Invergowrie AFC | 0 - 0 aet pens 3 - 2 | Morgan Academy FP |
| 4 | NCR AFC | 3 - 0 | Kelso AFC |
Semi Finals
| Carnoustie YM 'A' | 4 - 0 | Dundee University |
| Invergowrie AFC | 3 - 2 | NCR AFC |
Final
| Carnoustie YM 'A' | 1 - 2 aet | Invergowrie AFC |