Ferrari's Shield 2008-2009
(Presented by Ferrari's Bar,Dundee)
1st Round
| 1 | St James AFC | 5 - 0 | Kelso AFC |
| 2 | FC Claypotts | 1 - 1 aet pens 2 - 3 | Letham Lads Club |
| 3 | Caird Park AFC | 5 - 4 | Portcullis |
| 4 | Polepark AFC | 2 - 4 | Merpro AFC |
| 5 | Lowson United | 1 - 0 | Newport AFC |
2nd Round
| 1 | SS Peter & Paul | 1 - 8 | St James AFC |
| 2 | Dryburgh Athletic | 2 - 3 | Douglas Sports Club |
| 3 | Arbroath Harp | 1 - 1 aet pens 4 - 1 | Michelin Athletic |
| 4 | Merpro AFC | 5 - 1 | Monifieth Tayside |
| 5 | Caird Park AFC | 1 - 4 | Menzieshill AFC |
| 6 | Arbroath Amateurs | 0 - 5 | Lowson United |
| 7 | FC Polonia | 4 - 3 aet | Letham Lads Club |
| 8 | Logie Harp | 5 - 0 | Wellbank AFC |
Quarter Finals
| 1 | Menzieshill AFC | 3 - 2 aet | Lowson United |
| 2 | Logie Harp | 0 - 2 | Douglas Sports Club |
| 3 | Arbroath Harp | 3 - 4 | Merpro AFC |
| 4 | FC Polonia | 1 - 5 | St James AFC |
Semi Finals
| 1 | Merpro AFC | 1 - 7 | St James AFC |
| 2 | Menzieshill AFC | 3 - 1 | Douglas Sports Club |
FINAL
|
St James AFC |
2 - 3 |
Menzieshill AFC |
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