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MONTHLY DRAW
| MONTH | £40 WINNER | £25 WINNER | £15 WINNER |
| June 2010 | Arbroath Amateurs | Logie Harp | Dundee College |
| May 2010 | Carnoustie YM | Dundee University | SS Peter & Paul |
| April 2010 | Abroath Harp | Riverside Athletic | Merpro AFC |
| March 2010 | Castle AFC | Wellbank AFC | St Michaels AFC |
| February 2010 | St James AFC | PC Polonia Dundee | Arbroath Harp |
| January 2010 | NCR AFC | Invergowrie AFC | Lowson United |
| December 2009 | Dundee College | FC Claypotts | Merpro AFC |
| November 2009 | Barnhill AFC | Tayside Fire Brigade | Caird Park AFC |
| October 2009 | NCR AFC | Riverside Athletic | Portcullis AFC |
| September 2009 | Douglas SC | Harris Academy FP | Broughty United |
| June 2009 | NCR AFC | Portcullis AFC | FC Claypotts |
| May 2009 | Harris Academy FP | Tayside Fire Brigade | St Michaels AFC |
| April 2009 | St Michaels AFC | Polepark AFC | Harris Academy FP |
| March 2009 | Arbroath Harp | St Michaels AFC | Dryburgh Athletic |
| February 2009 | St James AFC | Bank Street Athletic | Riverside Athletic |
| January 2009 | Invergowrie AFC | NCR AFC | Merpro AFC |
| December 2008 | Broughty United | Monifieth Tayside | Douglas SC |
| November 2008 | Letham Lads Club | Broughty United | Polepark AFC |
| October 2008 | Tayside Fire Brigade | Michelin Athletic | Portcullis AFC |
| September 2008 | Elmwood AFC | Logie Harp | Polepark AFC |