| Round | Date | Step H | Home | HS | – | AS | Away | Step A |
|---|---|---|---|---|---|---|---|---|
| Prelim | Sat, Aug 30, 2025 | 3 | Dundee Violet | 5 | – | 0 | Blairgowrie | 3 |
| Prelim | Wed, Apr 29, 2026 | 3 | Montrose Roselea | 2 | – | 1 | Forfar United | 3 |
| 1st Round | Sat, May 2, 2026 | 3 | Montrose Roselea | 1 | – | 3 | Carnoustie Panmure | 2 |
| 1st Round | Sat, May 2, 2026 | 2 | Letham | 1p | – | 1 | Lochee Harp | 2 |
| 1st Round | Wed, May 6, 2026 | 3 | Arbroath Victoria | 3 | – | 4 | Downfield | 2 |
| 1st Round | Wed, May 6, 2026 | 2 | Broughty Athletic | 3 | – | 1 | Lochee United | 2 |
| 1st Round | Wed, May 13, 2026 | 3 | Dundee Violet | 0 | – | 3 | Tayport | 2 |
| 1st Round | Wed, May 13, 2026 | 2 | East Craigie | 2 | – | 3 | Forfar West End | 3 |
| 1st Round | Wed, May 13, 2026 | 2 | Kirriemuir Thistle | 1 | – | 3 | Dundee North End | 2 |
| 1st Round | Wed, May 13, 2026 | 3 | Scone Thistle | 0 | – | 2 | Dundee St James | 3 |
| Quarter Final | Sat, May 23, 2026 | 2 | Broughty Athletic | 11 | – | 0 | Dundee St James | 3 |
| Quarter Final | Sat, May 23, 2026 | 2 | Downfield | 7 | – | 2 | Forfar West End | 3 |
| Quarter Final | Sat, May 23, 2026 | 2 | Dundee North End | 4 | – | 1 | Tayport | 2 |
| Quarter Final | Sat, May 23, 2026 | 2 | Letham | 1 | – | 5 | Carnoustie Panmure | 2 |
| Semi Final | Wed, May 27, 2026 | 2 | Carnoustie Panmure | – | Downfield | 2 | ||
| Semi Final | Wed, May 27, 2026 | 2 | Broughty Athletic | – | Dundee North End | 2 | ||
| Final | Sat, May 30, 2026 | – |
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