| ROUND | R1 | R2 | QF | SF | F | ||||
| r1 | r2 | r3 | r4 | r5 | |||||
| Season archive |
| Group A | Overall | |||||||||||
| P | W | D | L | F | A | Gdf | Pts | Form | ||||
| 1 | 1 | Ayr United | 2 | 1 | 1 | 0 | 2 | 1 | +1 | 5 | WX-- | |
| 2 | 1 | Stirling Albion | 2 | 1 | 1 | 0 | 3 | 2 | +1 | 4 | WX-- | |
| 3 | 2 | Stenhousemuir | 2 | 1 | 0 | 1 | 1 | 1 | +0 | 3 | LW-- | |
| 4 | Alloa Athletic | 1 | 0 | 0 | 1 | 1 | 2 | -1 | 0 | L--- | ||
| 5 | St.Johnstone | 1 | 0 | 0 | 1 | 0 | 1 | -1 | 0 | L--- | ||
| Tuesday, 18 July 2023 | |||||
| 2 | Ayr United | 1-0 | Stenhousemuir | ||
| 27 | McKenzie | ||||
| 2 | Alloa Athletic | 1-2 | Stirling Albion | ||
| 62 | Coulson | 75 | McLean | ||
| 88(p) | Carrick | ||||
| Group B | Overall | |||||||||||
| P | W | D | L | F | A | Gdf | Pts | Form | ||||
| 1 | 1 | Partick Thistle | 2 | 1 | 1 | 0 | 3 | 2 | +1 | 5 | WX-- | |
| 2 | 2 | Falkirk | 1 | 1 | 0 | 0 | 2 | 1 | +1 | 3 | W--- | |
| 3 | 2 | Spartans | 2 | 1 | 0 | 1 | 2 | 2 | +0 | 3 | LW-- | |
| 4 | 1 | Peterhead | 1 | 0 | 1 | 0 | 1 | 1 | +0 | 1 | X--- | |
| 5 | Dundee United | 2 | 0 | 0 | 2 | 1 | 3 | -2 | 0 | LL-- | ||
| Tuesday, 18 July 2023 | |||||
| 2 | Dundee United | 1-2 | Partick Thistle | ||
| 18 | Sibbald | 32 | Graham | ||
| 58 | Milne | ||||
| 2 | Spartans | 1-2 | Falkirk | ||
| 60 | Henderson | 6 | Lang | ||
| 88 | MacIver | ||||
| Group C | Overall | |||||||||||
| P | W | D | L | F | A | Gdf | Pts | Form | ||||
| 1 | 1 | Hamilton | 2 | 2 | 0 | 0 | 4 | 1 | +3 | 6 | WW-- | |
| 2 | 1 | Cove Rangers | 1 | 1 | 0 | 0 | 5 | 2 | +3 | 3 | W--- | |
| 3 | 2 | Livingston | 1 | 1 | 0 | 0 | 3 | 0 | +3 | 3 | W--- | |
| 4 | 1 | Brechin City | 2 | 0 | 0 | 2 | 0 | 4 | -4 | 0 | LL-- | |
| 5 | 1 | Clyde | 2 | 0 | 0 | 2 | 3 | 8 | -5 | 0 | LL-- | |
| Tuesday, 18 July 2023 | |||||
| 2 | Hamilton | 1-0 | Brechin City | ||
| 22(p) | O'Hara | ||||
| 2 | Cove Rangers | 5-2 | Clyde | ||
| 13 | Connell | 20(p) | Rennie | ||
| 21 | Burrell | 84 | Mulvanny | ||
| 26 | Burrell | ||||
| 81 | Connell | ||||
| 83 | Megginson | ||||
| Group D | Overall | |||||||||||
| P | W | D | L | F | A | Gdf | Pts | Form | ||||
| 1 | 1 | Morton | 2 | 2 | 0 | 0 | 6 | 1 | +5 | 6 | WW-- | |
| 2 | 1 | Ross County | 1 | 1 | 0 | 0 | 5 | 1 | +4 | 3 | W--- | |
| 3 | 1 | Kelty Hearts | 2 | 1 | 0 | 1 | 6 | 6 | +0 | 3 | WL-- | |
| 4 | 1 | Edinburgh City | 1 | 0 | 0 | 1 | 3 | 5 | -2 | 0 | L--- | |
| 5 | Stranraer | 2 | 0 | 0 | 2 | 1 | 8 | -7 | 0 | LL-- | ||
| Tuesday, 18 July 2023 | |||||
| 2 | Morton | 3-0 | Stranraer | ||
| 22 | Baird | ||||
| 49 | Blues | ||||
| 73 | Crawford | ||||
| Wednesday, 19 July 2023 | |||||
| 2 | Edinburgh City | 3-5 | Kelty Hearts | ||
| 4 | Mercer | 27 | Johnston | ||
| 7 | McLean | 42 | Daramola | ||
| 20 | McLean | 45+3 | Daramola | ||
| 49 | Johnston | ||||
| 54 | Cunningham | ||||
| Group E | Overall | |||||||||||
| P | W | D | L | F | A | Gdf | Pts | Form | ||||
| 1 | Airdrieonians | 1 | 1 | 0 | 0 | 2 | 0 | +2 | 3 | W--- | ||
| 2 | 1 | Dundee | 1 | 1 | 0 | 0 | 1 | 0 | +1 | 3 | W--- | |
| 3 | 1 | Inverness CT | 2 | 1 | 0 | 1 | 3 | 3 | +0 | 3 | LW-- | |
| 4 | 1 | Dumbarton | 2 | 1 | 0 | 1 | 2 | 3 | -1 | 3 | WL-- | |
| 5 | 1 | Bonnyrigg Rose | 2 | 0 | 0 | 2 | 1 | 3 | -2 | 0 | LL-- | |
| Tuesday, 18 July 2023 | |||||
| 2 | Dumbarton | 2-1 | Inverness CT | ||
| 27 | Wallace | 76 | McKay | ||
| 50 | Wallace | ||||
| 2 | Bonnyrigg Rose | 0-1 | Dundee | ||
| 47 | Rudden | ||||
| Group F | Overall | |||||||||||
| P | W | D | L | F | A | Gdf | Pts | Form | ||||
| 1 | 1 | Dunfermline | 2 | 1 | 1 | 0 | 5 | 1 | +4 | 5 | WX-- | |
| 2 | 1 | Raith Rovers | 2 | 1 | 1 | 0 | 3 | 1 | +2 | 4 | WX-- | |
| 3 | 2 | Kilmarnock | 1 | 1 | 0 | 0 | 3 | 0 | +3 | 3 | W--- | |
| 4 | Albion Rovers | 1 | 0 | 0 | 1 | 0 | 2 | -2 | 0 | L--- | ||
| 5 | Annan Athletic | 2 | 0 | 0 | 2 | 0 | 7 | -7 | 0 | LL-- | ||
| Tuesday, 18 July 2023 | |||||
| 2 | Raith Rovers | 2-0 | Albion Rovers | ||
| 76 | Mullin | ||||
| 90+2(og) | |||||
| 2 | Dunfermline | 4-0 | Annan Athletic | ||
| 17 | Fisher | ||||
| 23(og) | Douglas | ||||
| 55 | McCann | ||||
| 59 | McCann | ||||
| Group G | Overall | |||||||||||
| P | W | D | L | F | A | Gdf | Pts | Form | ||||
| 1 | Motherwell | 2 | 1 | 1 | 0 | 5 | 3 | +2 | 5 | XW-- | ||
| 2 | East Fife | 2 | 1 | 1 | 0 | 3 | 1 | +2 | 5 | WO-- | ||
| 3 | 1 | Queen of the South | 1 | 0 | 1 | 0 | 3 | 3 | +0 | 1 | X--- | |
| 4 | 1 | Queen's Park | 1 | 0 | 1 | 0 | 0 | 0 | +0 | 1 | O--- | |
| 5 | Elgin City | 2 | 0 | 0 | 2 | 1 | 5 | -4 | 0 | LL-- | ||
| Tuesday, 18 July 2023 | |||||
| 2 | East Fife | 3-1 | Elgin City | ||
| 2 | Austin | 77 | Dingwall | ||
| 39 | Austin | ||||
| 79 | Austin | ||||
| 2 | Queen of the South | 3-3 | Motherwell | ||
| 18 | McKechnie | 40 | Spittal | ||
| 73 | Reilly | 56 | Slattery | ||
| 83(p) | Reilly | 75 | Spittal | ||
| Group H | Overall | |||||||||||
| P | W | D | L | F | A | Gdf | Pts | Form | ||||
| 1 | 1 | Forfar Athletic | 2 | 2 | 0 | 0 | 3 | 1 | +2 | 6 | WW-- | |
| 2 | 1 | Montrose | 2 | 1 | 0 | 1 | 2 | 2 | +0 | 3 | LW-- | |
| 3 | Arbroath | 1 | 0 | 1 | 0 | 1 | 1 | +0 | 2 | X--- | ||
| 4 | Cowdenbeath | 2 | 0 | 1 | 1 | 1 | 2 | -1 | 1 | XL-- | ||
| 5 | St.Mirren | 1 | 0 | 0 | 1 | 0 | 1 | -1 | 0 | L--- | ||
| Tuesday, 18 July 2023 | |||||
| 2 | Montrose | 1-2 | Forfar Athletic | ||
| 56 | Hester | 34(p) | Skelly | ||
| 40 | Ross | ||||
| Wednesday, 19 July 2023 | |||||
| 2 | Arbroath | 1-1 | Cowdenbeath | ||
| 51(p) | McKenna | 61 | |||
| 3 | +3 | Nathan AUSTIN (East Fife) |
| Simon MURRAY (Ross County) | ||
| +2 | Lewis McCANN (Dunfermline) | |
| +2 | Tiwi DARAMOLA (Kelty Hearts) | |
| 2 | +2 | Kyle CONNELL (Cove Rangers) |
| Aaron DORAN (Inverness CT) | ||
| +1 | Robbie CRAWFORD (Morton) | |
| +2 | Craig JOHNSTON (Kelty Hearts) | |
| +1 | Harry MILNE (Partick Thistle) | |
| +2 | Russell McLEAN (Edinburgh City) | |
| +1 | Blair HENDERSON (Spartans) | |
| +2 | Blair SPITTAL (Motherwell) | |
| +2 | Rumarn BURRELL (Cove Rangers) | |
| +2 | Gavin REILLY (Queen of the South) |