Bremner Challenge Cup 2008-2009
(Presented by WSC Bremner)
(Sponsored by NCR FINANCIAL SERVICES GROUP)
1st Round
| 1 | Newport AFC | 1 - 2 | St James AFC |
| 2 | Menzieshill AFC | 3 - 4 aet | Arbroath HSFP |
| 3 | Portcullis AFC | 3 - 0 | Dryburgh AFC |
| 4 | Douglas Sports Club | 2 - 1 | Michelin Athletic |
| 5 | Tayside Fire Brigade | 4 - 2 | FC Claypotts |
2nd Round
| 1 | Arbroath Harp | 0 - 6 | Invergowrie AFC |
| 2 | Monifieth Tayside | 1 - 4 | Harris Academy |
| 3 | St James AFC | 2 - 2 aet pens 5 - 6 | Tayside Fire Brigade |
| 4 | Elmwood AFC | 2 - 0 | Logie Harp AFC |
| 5 | Dundee College | 3 - 2 | FC Polonia Dundee |
| 6 | Douglas Sports Club | 3 - 4 | Riverside Athletic |
| 7 | Letham Lads Club | 0 - 1 | Barnhill AFC |
| 8 | Portcullis AFC | frft - w/o | NCR AFC |
| 9 | SS Peter & Paul | 1 - 3 | Broughty United |
| 10 | St Michaels AFC | w/o - frft | Caird Park AFC |
| 11 | Dundee Shamrock | 4 - 1 | Polepark AFC |
| 12 | Morgan Academy FP | 5 - 0 | Wellbank AFC |
| 13 | Arbroath Amateurs | 1 - 1 aet pens 5 - 6 | Arbroath HSFP |
| 14 | Dundee University | 4 - 0 | Merpro AFC |
| 15 | Kelso AFC | 0 - 4 | Carnoustie YM |
| 16 | Lowson United | 1 - 2 | Bank Street Athletic |
3rd Round
| 1 | Dundee University | 2 - 3 aet | Tayside Fire Brigade |
| 2 | Arbroath HSFP | 0 - 1 aet | Broughty United |
| 3 | NCR AFC | 0 - 2 | Riverside Athletic |
| 4 | St Michaels AFC | 0 - 5 | Morgan Academy FP |
| 5 | Carnoustie YM | 0 - 1 aet | Invergowrie AFC |
| 6 | Bank Street Athletic | 2 - 1 aet | Barnhill AFC |
| 7 | Dundee College | 6 - 2 | Dundee Shamrock |
| 8 | Harris Academy | 0 - 5 | Elmwood AFC |
Quarter Finals
| 1 | Riverside Athletic | 1 - 2 | Bank Street Athletic |
| 2 | Dundee College | 0 - 2 | Elmwood AFC |
| 3 | Broughty United | 1 - 2 | Morgan Academy FP |
| 4 | Tayside Fire Brigade | 2 - 1 aet | Invergowrie AFC |
Semi Finals
| 1 | Bank Street Athletic | w/o - disq | Morgan Academy FP |
| 2 | Elmwood AFC | 3 - 1 | Tayside Fire Brigade |
Final
| Bank Street Athletic | 2 - 1 | Elmwood AFC |
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