| 23.12.20082008-12-23 20:45:00 | 20:45 | Tennents Scottish Cup | 3. R | Ayr United - Lochee United | 3:1 (1:0) |
| 17.12.20082008-12-17 14:30:00 | 14:30 | Tennents Scottish Cup | 3. R | Lochee United - Ayr United | 1:1 (0:0) |
| 25.10.20082008-10-25 15:30:00 | 15:30 | Tennents Scottish Cup | 2. R | Lochee United - Buckie Thistle | 3:0 (1:0) |
| 27.9.20082008-9-27 15:30:00 | 15:30 | Tennents Scottish Cup | 1. R | Lochee United - Bathgate Thistle | 3:1 |
| 27.9.20082008-9-27 15:30:00 | 15:30 | Tennents Scottish Cup | 1. R | Lochee United - Bathgate Thistle | 3:1 |