| Round | Date | Step H | Home | HS | – | AS | Away | Step A |
|---|---|---|---|---|---|---|---|---|
| 1st Round (Midland) | Sat, Oct 11, 2025 | 2 | Broughty Athletic | 6 | v | 1 | Letham | 2 |
| 1st Round (Midland) | Sat, Oct 11, 2025 | 2 | Downfield | 3 | v | 2 | Dundee St James | 3 |
| 1st Round (Midland) | Sat, Oct 11, 2025 | 2 | Dundee North End | 2 | v | 0 | Carnoustie Panmure | 2 |
| 1st Round (Midland) | Sat, Oct 11, 2025 | 2 | Lochee United | 2 | v | 1 | Scone Thistle | 3 |
| 1st Round (North) | Sat, Nov 1, 2025 | 2 | Aberdeen East End | 2 | v | 4 | Stonehaven | 2 |
| 1st Round (North) | Sat, Nov 1, 2025 | 3 | Banchory St Ternan | 3 | v | 0 | Fraserburgh United | 3 |
| 1st Round (North) | Sat, Nov 1, 2025 | 2 | Colony Park | 6 | v | 2 | Nairn St Ninian | 3 |
| 1st Round (North) | Sat, Nov 1, 2025 | 2 | Culter | 5 | v | 1 | Banks O Dee Juniors | 2 |
| 1st Round (North) | Sat, Nov 1, 2025 | 3 | Deveronside | 1 | v | 3 | Rothie Rovers | 2 |
| 1st Round (North) | Sat, Nov 1, 2025 | 2 | Dyce | 1 | v | 0 | Dufftown | 3 |
| 1st Round (North) | Sat, Nov 1, 2025 | 3 | Glentanar | 0 | v | 5 | Bridge of Don Thistle | 2 |
| 1st Round (North) | Sat, Nov 1, 2025 | 2 | Islavale | 2 | v | 2p | Hall Russell United | 3 |
| 1st Round (North) | Sat, Nov 1, 2025 | 2 | Longside | 2 | v | 8 | Hermes | 2 |
| 1st Round (North) | Sat, Nov 1, 2025 | 2 | Maud | 10 | v | 1 | Cruden Bay | 3 |
| 1st Round (North) | Sat, Nov 1, 2025 | 3 | Stoneywood Parkvale | 5 | v | 0 | Sunnybank | 2 |
| 2nd Round (Midland) | Sat, Oct 11, 2025 | 3 | Dundee Violet | 1 | v | 0 | Coupar Angus | 3 |
| 2nd Round (Midland) | Sat, Oct 11, 2025 | 3 | Forfar West End | 1p | v | 1 | East Craigie | 2 |
| 2nd Round (Midland) | Sat, Oct 11, 2025 | 2 | Lochee Harp | 1 | v | 0 | Forfar United | 3 |
| 2nd Round (Midland) | Sat, Oct 11, 2025 | 2 | Tayport | 4 | v | 2 | Kirriemuir Thistle | 2 |
| 2nd Round (Midland) | Sat, Nov 8, 2025 | 3 | Arbroath Victoria | 0 | v | 0p | Brechin Victoria | 3 |
| 2nd Round (Midland) | Sat, Nov 8, 2025 | 2 | Downfield | 4 | v | 1 | Montrose Roselea | 3 |
| 2nd Round (Midland) | Sat, Nov 8, 2025 | 2 | Dundee North End | 6 | v | 0 | Blairgowrie | 3 |
| 2nd Round (Midland) | Sat, Nov 8, 2025 | 2 | Lochee United | 1 | v | 1p | Broughty Athletic | 2 |
| 2nd Round (North) | Sat, Dec 6, 2025 | 2 | Bridge of Don Thistle | 0 | v | 4 | Culter | 2 |
| 2nd Round (North) | Sat, Dec 6, 2025 | 2 | Dyce | 3 | v | 0 | Stoneywood Parkvale | 3 |
| 2nd Round (North) | Sat, Dec 6, 2025 | 2 | Ellon United | 0 | v | 2 | Stonehaven | 2 |
| 2nd Round (North) | Sat, Dec 6, 2025 | 3 | Hall Russell United | 0p | v | 0 | Forres Thistle | 3 |
| 2nd Round (North) | Sat, Dec 6, 2025 | 2 | Hermes | 3 | v | 0 | Banchory St Ternan | 3 |
| 2nd Round (North) | Sat, Dec 6, 2025 | 3 | Westdyke | 0 | v | 4 | Maud | 2 |
| 2nd Round (North) | Sat, Feb 21, 2026 | 2 | Colony Park | 2 | v | 1 | Buchanhaven Hearts | 2 |
| 2nd Round (North) | Sat, Feb 21, 2026 | 2 | Rothie Rovers | 5 | v | 3 | Newmachur United | 3 |
| 3rd Round | Sat, Mar 7, 2026 | 3 | Brechin Victoria | 0 | v | 3 | Hall Russell United | 3 |
| 3rd Round | Sat, Mar 7, 2026 | 2 | Colony Park | 1 | v | 2 | Broughty Athletic | 2 |
| 3rd Round | Sat, Mar 7, 2026 | 2 | Dundee North End | 3 | v | 0 | Rothie Rovers | 2 |
| 3rd Round | Sat, Mar 7, 2026 | 3 | Dundee Violet | 0 | v | 3 | Culter | 2 |
| 3rd Round | Sat, Mar 7, 2026 | 2 | Dyce | 0 | v | 1 | Downfield | 2 |
| 3rd Round | Sat, Mar 7, 2026 | 2 | Hermes | 0 | v | 1 | Lochee Harp | 2 |
| 3rd Round | Sat, Mar 7, 2026 | 2 | Maud | 4 | v | 2 | Forfar West End | 3 |
| 3rd Round | Sat, Mar 7, 2026 | 2 | Tayport | 0 | v | 3 | Stonehaven | 2 |
| Quarter Final | Sat, Apr 4, 2026 | 2 | Broughty Athletic | 5 | v | 1 | Lochee Harp | 2 |
| Quarter Final | Sat, Apr 4, 2026 | 2 | Culter | 5 | v | 0 | Hall Russell United | 3 |
| Quarter Final | Sat, Apr 4, 2026 | 2 | Downfield | 3 | v | 2 | Maud | 2 |
| Quarter Final | Sat, Apr 4, 2026 | 2 | Stonehaven | 0 | v | 3 | Dundee North End | 2 |
| Semi Final | Sat, May 2, 2026 | 2 | Culter | 2 | v | 1 | Broughty Athletic | 2 |
| Semi Final | Sat, May 2, 2026 | 2 | Downfield | 0 | v | 3 | Dundee North End | 2 |
| Final | Sat, May 16, 2026 | 2 | Culter | 2 | v | 3 | Dundee North End | 2 |
| CHAMPIONS | Sat, Aug 1, 2026 | DUNDEE NORTH END |
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