| Round | Date | Step H | Home | HS | – | AS | Away | Step A |
|---|---|---|---|---|---|---|---|---|
| 1st Round | Wed, Aug 14, 2024 | 2 | Brechin Victoria | 0 | – | 1 | Kirriemuir Thistle | 2 |
| 1st Round | Wed, Aug 14, 2024 | 2 | East Craigie | 5 | – | 0 | Montrose Roselea | 2 |
| 1st Round | Wed, Aug 14, 2024 | 2 | Forfar United | 0 | – | 4 | Dundee st James | 2 |
| 1st Round | Wed, Aug 14, 2024 | 2 | Tayport | 2 | – | 0 | Blairgowrie | 2 |
| 2nd Round | Wed, Aug 21, 2024 | 2 | Kirriemuir Thistle | 2 | – | 3 | Downfield | 2 |
| 2nd Round | Wed, Aug 21, 2024 | 2 | Broughty Athletic | 1 | – | 4 | Dundee North End | 2 |
| 2nd Round | Wed, Aug 21, 2024 | 2 | Carnoustie Panmure | 0 | – | 3 | East Craigie | 2 |
| 2nd Round | Wed, Aug 21, 2024 | 2 | Forfar West End | 0 | – | 6 | Lochee United | 2 |
| 2nd Round | Wed, Aug 21, 2024 | 2 | Letham | 0 | – | 1 | Coupar Angus | 2 |
| 2nd Round | Wed, Aug 21, 2024 | 2 | Lochee Harp | 3 | – | 0 | Arbroath Victoria | 2 |
| 2nd Round | Wed, Aug 21, 2024 | 2 | Scone Thistle | 1p | – | 1 | Dundee Violet | 2 |
| 2nd Round | Wed, Aug 21, 2024 | 2 | Tayport | 4 | – | 2 | Dundee St James | 2 |
| Quarter Finals | Sat, Feb 15, 2025 | 2 | Lochee Harp | 1 | – | 2 | Coupar Angus | 2 |
| Quarter Finals | Sat, Feb 15, 2025 | 2 | Tayport | 1 | – | 2 | Lochee United | 2 |
| Quarter Finals | Wed, Apr 23, 2025 | 2 | East Craigie | – | Dundee North End | 2 | ||
| Quarter Finals | Wed, Apr 23, 2025 | 2 | Scone Thistle | – | Downfield | 2 | ||
| Semi Final | ||||||||
| Semi Final | – | |||||||
| Final |