| 1 | Ballinluig AFC | v | Morgan Academy FP |
| 2 | Logie Harp | v | Portcullis AFC |
| 3 | Cannon Fodder FC | 1 - 3 | NCR AFC |
| 4 | Dundee Accies | 1 - 3 | Tayside Royal FC |
| 5 | Comrie Rovers | 2 - 3 aet | Invergowrie AFC |
| 6 | Arbroath HSFP | 2 - 0 | Auchterarder Primrose |
| 7 | Lowson United | 1 - 3 | Dundee College |
| 8 | Bank Street Athletic | 4 - 1 | Letham Lads Club |
| 9 | Elmwood AFC | 0 - 4 | Burrleton Rovers |
| 10 | Caird Park AFC | 6 - 3 aet | Letham Amateurs |
| 11 | St Michaels AFC | 1 - 2 | Letham Lads (Perth) |
| 12 | Kelso AFC | 4 - 5 aet | St James AFC |
| 13 | Broughty United | 8 - 0 | Menzieshill AFC |
| 14 | Breadalbane |
10 - 0 |
Riverside Plate |
| 15 | Riverside Athletic | v | Roselea AFC |
| 16 | Carnoustie YM | 1 - 2 | St Johns AFC |
Ties to be played on or before 28 November 2009
ROUND 1
Ties to be played on or before 26 September 2009
| 1 | Invergowrie AFC | 3 - 1 | Perth Villareal |
| 2 | Barnhill AFC | 1 - 4 | Riverside Athletic |
| 3 | St Johns AFC | 3 - 2 | FC Claypotts AFC |
| 4 | Wolfhill AFC | 3 - 5 | Kinross AFC |
| 5 | Arbroath Harp | 1 - 3 | Arbroath HSFP |
| 6 | Monifieth Tayside | 0 - 6 | Burrleton Rovers |
| 7 | Meigle Vics | 0 - 2 | Portcullis AFC |
| 8 | Michelin Athletic |
5 - 8 AET |
Logie Harp |
| 9 | Vale of Atholl | 2 - 5 | Roselea AFC |
| 10 | Caird Park AFC | 10 - 4 | Tay Thistle |
| 11 | Fair City AFC | 2 - 3 | Fairfield AFC |
ROUND 2
| 1 | Letham Lads Club | 4 - 2 | Wellbank AFC |
| 2 | Letham Lads (Perth) | 2 - 3 | Douglas Sports Club |
| 3 | Coupar Angus AFC | 1 - 3 | Comrie Rovers |
| 4 | Errol Rovers | 0 -11 | Auchterarder Primrose |
| 5 | Newtyle Hearts | 0 - 2 | NCR AFC |
| 6 | Logie Harp | 3 - 0 | Bridgeton AFC |
| 7 | Parktool Athletic FC | 1 - 4 | St Michaels AFC |
| 8 | Kinrossie Caledonian | 0 - 7 | St James AFC |
| 9 | Merpro AFC | 2 - 6 | Tayside Royal FC |
| 10 | Carnoustie YM | w/o - dis | Kinross AFC |
| 11 | Portcullis AFC | 4 - 2 aet | Harris Academy FP |
| 12 | Breadalbane AFC | 7 - 1 | FC Polonia Dundee |
| 13 | St Johns AFC | 2 - 1 | Dundee University |
| 14 | Methven AFC |
1 - 4 |
Broughty United |
| 15 | Arbroath HSFP | 5 - 1 | Dundee Medical Students |
| 16 | Elmwood AFC | 4 - 2 | Alyth Amateurs |
| 17 | Burrleton Rovers | 5 - 1 | Dryburgh Athletic |
| 18 | Menzieshill AFC | 8 - 1 | Fairfield AFC |
| 19 | Bank Street Athletic | 2 - 1aet | Tayside Fire Brigade |
| 20 | Bridge of Earn | 2 - 9 | Riverside Athletic |
| 21 | Riverside Plate | 4 - 0 | Letham United |
| 22 | Craigie FC | 2 - 3 | Cannon Fodder FC |
| 23 | Arbroath Amateurs | 0 - 1 | Roselea AFC |
| 24 | Lowson United | 4 - 1 | Strathearn Grove FC |
| 25 | Dundee Shamrock | scr - w/o | Dundee Accies |
| 26 | Balmoral United | 1 - 4 | Morgan Academy FP |
| 27 | Kettins AFC | 2 - 3 | Ballinluig AFC |
| 28 | Letham Amateurs | 4 - 3 | Vale Of Earn |
| 29 | Invergowrie AFC | 4 - 0 | Star of Atholl |
| 30 | Kelso AFC | 3 - 0 | Rattray AFC |
| 31 | Dundee College | 5 - 2 | DC Athletic |
| 32 | Taybank AFC | 1 - 6 | Caird Park AFC |