Results
|
| Lochore Welfare | 0 - 4 | Kirkcaldy YM | 6/03/10 | 2:30pm | Read Report |
| Lochgelly Albert | 1 - 4 | Kirkcaldy YM | 20/02/10 | 2:15pm | |
| Dalkeith Thistle | 2 - 5 | Kirkcaldy YM | 13/02/10 | 2:15pm | Read Report |
| Kirkcaldy YM | 9 - 1 | Luncarty | 23/01/10 | 1:45pm | Read Report |
| Kirkcaldy YM | 2 - 0 | Scone Thistle | 12/12/09 | 1:45pm | Read Report |
| Arthurlie | 6 - 0 | Kirkcaldy YM | 28/11/09 | 2:00pm | Read Report |
| Kirkcaldy YM | 3 - 1 | Bankfoot | 21/11/09 | 2:00pm | Read Report |
| Boness United | 8 - 1 | Kirkcaldy YM | 14/11/09 | 2:00pm | |
| Kirkcaldy YM | 5 - 0 | Arbroath Sporting Club | 31/10/09 | 2:00pm | |
| Kirkcaldy YM | 1 - 1 | Lochore Welfare | 24/10/09 | 2:30pm | |
| Haddington Athletic | 0 - 1 | Kirkcaldy YM | 17/10/09 | 2:30pm | |
| Kirkcaldy YM | 3 - 2 | Rosyth | 10/10/09 | 2:30pm | |
| Kirkcaldy YM | 2 - 0 | Jeanfield Swifts | 3/10/09 | 3:00pm | |
| Dundee North End | 1 - 1 | Kirkcaldy YM | 26/09/09 | 2:30pm | |
| YM win on penalties |
| Jeanfield Swifts | 0 - 2 | Kirkcaldy YM | 19/09/09 | 2:30pm | |
| Kirkcaldy YM | 6 - 2 | Crossgates Primrose | 12/09/09 | 2:30pm | |
| Oakley United | 1 - 0 | Kirkcaldy YM | 5/09/09 | 2:30pm | |
| Kirkcaldy YM | 1 - 2 | Thornton Hibs | 29/08/09 | 2:30pm | |
| Glenrothes | 3 - 2 | Kirkcaldy YM | 19/08/09 | 6:45pm | |
| Thornton Hibs | 3 - 0 | Kirkcaldy YM | 15/08/09 | 2:30pm | |
| Kirkcaldy YM | 1 - 0 | St Andrews United | 12/08/09 | 6:45pm | |
| Kirkcaldy YM | 3 - 1 | Newburgh | 8/08/09 | 2:30am | |
