| 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 | Ayr United | 4 | 3 | 1 | 0 | 10 | 2 | +8 | 11 | WWWX | ||
| 2 | Stirling Albion | 4 | 3 | 1 | 0 | 9 | 3 | +6 | 10 | WWWX | ||
| 3 | St.Johnstone | 4 | 1 | 0 | 3 | 5 | 7 | -2 | 3 | LLWL | ||
| 4 | Stenhousemuir | 4 | 1 | 0 | 3 | 3 | 6 | -3 | 3 | LLLW | ||
| 5 | Alloa Athletic | 4 | 1 | 0 | 3 | 4 | 13 | -9 | 3 | LWLL | ||
| Saturday, 15 July 2023 | |||||
| 1 | Stirling Albion | 1-1 | Ayr United | ||
| 1 | Stenhousemuir | 1-0 | St.Johnstone | ||
| Tuesday, 18 July 2023 | |||||
| 2 | Ayr United | 1-0 | Stenhousemuir | ||
| 2 | Alloa Athletic | 1-2 | Stirling Albion | ||
| Saturday, 22 July 2023 | |||||
| 3 | Stirling Albion | 2-1 | Stenhousemuir | ||
| 3 | Alloa Athletic | 0-4 | St.Johnstone | ||
| Tuesday, 25 July 2023 | |||||
| 4 | St.Johnstone | 1-2 | Ayr United | ||
| 4 | Stenhousemuir | 1-3 | Alloa Athletic | ||
| Saturday, 29 July 2023 | |||||
| 5 | St.Johnstone | 0-4 | Stirling Albion | ||
| 5 | Ayr United | 6-0 | Alloa Athletic | ||
| Group B | Overall | |||||||||||
| P | W | D | L | F | A | Gdf | Pts | Form | ||||
| 1 | Partick Thistle | 4 | 2 | 2 | 0 | 7 | 5 | +2 | 9 | WXWX | ||
| 2 | Falkirk | 4 | 2 | 1 | 1 | 8 | 5 | +3 | 8 | WLXW | ||
| 3 | Dundee United | 4 | 2 | 0 | 2 | 5 | 3 | +2 | 6 | WWLL | ||
| 4 | Spartans | 4 | 2 | 0 | 2 | 5 | 5 | +0 | 6 | LWLW | ||
| 5 | Peterhead | 4 | 0 | 1 | 3 | 3 | 10 | -7 | 1 | LLLX | ||
| Saturday, 15 July 2023 | |||||
| 1 | Peterhead | 1-1 | Partick Thistle | ||
| 1 | Spartans | 1-0 | Dundee United | ||
| Tuesday, 18 July 2023 | |||||
| 2 | Dundee United | 1-2 | Partick Thistle | ||
| 2 | Spartans | 1-2 | Falkirk | ||
| Saturday, 22 July 2023 | |||||
| 3 | Dundee United | 3-0 | Peterhead | ||
| 3 | Partick Thistle | 2-2 | Falkirk | ||
| Tuesday, 25 July 2023 | |||||
| 4 | Falkirk | 0-1 | Dundee United | ||
| Wednesday, 26 July 2023 | |||||
| 4 | Peterhead | 1-2 | Spartans | ||
| Saturday, 29 July 2023 | |||||
| 5 | Falkirk | 4-1 | Peterhead | ||
| 5 | Partick Thistle | 2-1 | Spartans | ||
| Group C | Overall | |||||||||||
| P | W | D | L | F | A | Gdf | Pts | Form | ||||
| 1 | Livingston | 4 | 3 | 1 | 0 | 10 | 1 | +9 | 10 | WWXW | ||
| 2 | Hamilton | 4 | 2 | 2 | 0 | 7 | 4 | +3 | 9 | XXWW | ||
| 3 | Cove Rangers | 4 | 2 | 1 | 1 | 10 | 11 | -1 | 8 | XLWW | ||
| 4 | Brechin City | 4 | 1 | 0 | 3 | 4 | 8 | -4 | 3 | WLLL | ||
| 5 | Clyde | 4 | 0 | 0 | 4 | 4 | 11 | -7 | 0 | LLLL | ||
| Saturday, 15 July 2023 | |||||
| 1 | Clyde | 1-3 | Hamilton | ||
| 1 | Brechin City | 0-3 | Livingston | ||
| Tuesday, 18 July 2023 | |||||
| 2 | Hamilton | 1-0 | Brechin City | ||
| 2 | Cove Rangers | 5-2 | Clyde | ||
| Saturday, 22 July 2023 | |||||
| 3 | Livingston | 1-1 | Hamilton | ||
| 3 | Brechin City | 2-3 | Cove Rangers | ||
| Tuesday, 25 July 2023 | |||||
| 4 | Clyde | 1-2 | Brechin City | ||
| 4 | Cove Rangers | 0-5 | Livingston | ||
| Saturday, 29 July 2023 | |||||
| 5 | Hamilton | 2-2 | Cove Rangers | ||
| 5 | Livingston | 1-0 | Clyde | ||
| Group D | Overall | |||||||||||
| P | W | D | L | F | A | Gdf | Pts | Form | ||||
| 1 | Ross County | 4 | 3 | 1 | 0 | 13 | 6 | +7 | 10 | XWWW | ||
| 2 | Morton | 4 | 3 | 0 | 1 | 11 | 4 | +7 | 9 | WLWW | ||
| 3 | Kelty Hearts | 4 | 2 | 1 | 1 | 11 | 9 | +2 | 8 | XWWL | ||
| 4 | Stranraer | 4 | 1 | 0 | 3 | 3 | 11 | -8 | 3 | LWLL | ||
| 5 | Edinburgh City | 4 | 0 | 0 | 4 | 6 | 14 | -8 | 0 | LLLL | ||
| Saturday, 15 July 2023 | |||||
| 1 | Stranraer | 1-5 | Ross County | ||
| 1 | Kelty Hearts | 1-3 | Morton | ||
| Tuesday, 18 July 2023 | |||||
| 2 | Morton | 3-0 | Stranraer | ||
| Wednesday, 19 July 2023 | |||||
| 2 | Edinburgh City | 3-5 | Kelty Hearts | ||
| Saturday, 22 July 2023 | |||||
| 3 | Stranraer | 2-1 | Edinburgh City | ||
| 3 | Ross County | 2-1 | Morton | ||
| Tuesday, 25 July 2023 | |||||
| 4 | Kelty Hearts | 2-0 | Stranraer | ||
| Wednesday, 26 July 2023 | |||||
| 4 | Edinburgh City | 1-3 | Ross County | ||
| Saturday, 29 July 2023 | |||||
| 5 | Morton | 4-1 | Edinburgh City | ||
| 5 | Ross County | 3-3 | Kelty Hearts | ||
| Group E | Overall | |||||||||||
| P | W | D | L | F | A | Gdf | Pts | Form | ||||
| 1 | Airdrieonians | 4 | 4 | 0 | 0 | 7 | 2 | +5 | 12 | WWWW | ||
| 2 | Dundee | 4 | 3 | 0 | 1 | 5 | 2 | +3 | 9 | WWLW | ||
| 3 | Dumbarton | 4 | 1 | 1 | 2 | 3 | 6 | -3 | 5 | LOWL | ||
| 4 | Inverness CT | 4 | 1 | 0 | 3 | 5 | 7 | -2 | 3 | LLLW | ||
| 5 | Bonnyrigg Rose | 4 | 0 | 1 | 3 | 1 | 4 | -3 | 1 | LOLL | ||
| Saturday, 15 July 2023 | |||||
| 1 | Airdrieonians | 2-0 | Dumbarton | ||
| 1 | Inverness CT | 2-1 | Bonnyrigg Rose | ||
| Tuesday, 18 July 2023 | |||||
| 2 | Dumbarton | 2-1 | Inverness CT | ||
| 2 | Bonnyrigg Rose | 0-1 | Dundee | ||
| Saturday, 22 July 2023 | |||||
| 3 | Airdrieonians | 1-0 | Dundee | ||
| 3 | Dumbarton | 0-0 | Bonnyrigg Rose | ||
| Tuesday, 25 July 2023 | |||||
| 4 | Inverness CT | 2-3 | Airdrieonians | ||
| Wednesday, 26 July 2023 | |||||
| 4 | Dundee | 3-1 | Dumbarton | ||
| Saturday, 29 July 2023 | |||||
| 5 | Bonnyrigg Rose | 0-1 | Airdrieonians | ||
| Sunday, 30 July 2023 | |||||
| 5 | Dundee | 1-0 | Inverness CT | ||
| Group F | Overall | |||||||||||
| P | W | D | L | F | A | Gdf | Pts | Form | ||||
| 1 | Kilmarnock | 4 | 3 | 1 | 0 | 9 | 3 | +6 | 10 | WXWW | ||
| 2 | Raith Rovers | 4 | 2 | 2 | 0 | 8 | 5 | +3 | 9 | WXWX | ||
| 3 | Dunfermline | 4 | 2 | 1 | 1 | 8 | 3 | +5 | 8 | WLWX | ||
| 4 | Albion Rovers | 4 | 1 | 0 | 3 | 3 | 8 | -5 | 3 | LLWL | ||
| 5 | Annan Athletic | 4 | 0 | 0 | 4 | 3 | 12 | -9 | 0 | LLLL | ||
| Saturday, 15 July 2023 | |||||
| 1 | Raith Rovers | 1-1 | Dunfermline | ||
| 1 | Kilmarnock | 3-0 | Annan Athletic | ||
| Tuesday, 18 July 2023 | |||||
| 2 | Raith Rovers | 2-0 | Albion Rovers | ||
| 2 | Dunfermline | 4-0 | Annan Athletic | ||
| Saturday, 22 July 2023 | |||||
| 3 | Dunfermline | 0-2 | Kilmarnock | ||
| 4 | Annan Athletic | 1-2 | Albion Rovers | ||
| Tuesday, 25 July 2023 | |||||
| 4 | Albion Rovers | 0-3 | Dunfermline | ||
| Wednesday, 26 July 2023 | |||||
| 4 | Kilmarnock | 2-2 | Raith Rovers | ||
| Saturday, 29 July 2023 | |||||
| 5 | Albion Rovers | 1-2 | Kilmarnock | ||
| 5 | Annan Athletic | 2-3 | Raith Rovers | ||
| Group G | Overall | |||||||||||
| P | W | D | L | F | A | Gdf | Pts | Form | ||||
| 1 | Motherwell | 4 | 3 | 1 | 0 | 9 | 3 | +6 | 11 | WWXW | ||
| 2 | Queen of the South | 4 | 2 | 2 | 0 | 7 | 4 | +3 | 8 | WOWX | ||
| 3 | East Fife | 4 | 1 | 2 | 1 | 3 | 4 | -1 | 7 | LOWO | ||
| 4 | Queen's Park | 4 | 1 | 1 | 2 | 6 | 3 | +3 | 4 | LWLO | ||
| 5 | Elgin City | 4 | 0 | 0 | 4 | 1 | 12 | -11 | 0 | LLLL | ||
| Saturday, 15 July 2023 | |||||
| 1 | East Fife | 0-0 | Queen's Park | ||
| 1 | Elgin City | 0-2 | Motherwell | ||
| Tuesday, 18 July 2023 | |||||
| 2 | East Fife | 3-1 | Elgin City | ||
| 2 | Queen of the South | 3-3 | Motherwell | ||
| Saturday, 22 July 2023 | |||||
| 3 | Motherwell | 1-0 | Queen's Park | ||
| 3 | Elgin City | 0-2 | Queen of the South | ||
| Tuesday, 25 July 2023 | |||||
| 4 | Queen's Park | 5-0 | Elgin City | ||
| 4 | Queen of the South | 0-0 | East Fife | ||
| Saturday, 29 July 2023 | |||||
| 5 | Motherwell | 3-0 | East Fife | ||
| 5 | Queen's Park | 1-2 | Queen of the South | ||
| Group H | Overall | |||||||||||
| P | W | D | L | F | A | Gdf | Pts | Form | ||||
| 1 | St.Mirren | 4 | 3 | 0 | 1 | 9 | 1 | +8 | 9 | WWWL | ||
| 2 | Forfar Athletic | 4 | 3 | 0 | 1 | 6 | 6 | +0 | 9 | LWWW | ||
| 3 | Arbroath | 4 | 1 | 1 | 2 | 5 | 8 | -3 | 5 | WLLX | ||
| 4 | Montrose | 4 | 1 | 1 | 2 | 3 | 6 | -3 | 5 | LXLW | ||
| 5 | Cowdenbeath | 4 | 0 | 2 | 2 | 2 | 4 | -2 | 2 | LXXL | ||
| Saturday, 15 July 2023 | |||||
| 1 | Forfar Athletic | 1-0 | Cowdenbeath | ||
| 1 | Montrose | 1-0 | St.Mirren | ||
| Tuesday, 18 July 2023 | |||||
| 2 | Montrose | 1-2 | Forfar Athletic | ||
| Wednesday, 19 July 2023 | |||||
| 2 | Arbroath | 1-1 | Cowdenbeath | ||
| Saturday, 22 July 2023 | |||||
| 3 | St.Mirren | 4-0 | Arbroath | ||
| 3 | Cowdenbeath | 1-1 | Montrose | ||
| Tuesday, 25 July 2023 | |||||
| 4 | Cowdenbeath | 0-1 | St.Mirren | ||
| 4 | Forfar Athletic | 3-1 | Arbroath | ||
| Saturday, 29 July 2023 | |||||
| 5 | St.Mirren | 4-0 | Forfar Athletic | ||
| 5 | Arbroath | 3-0 | Montrose | ||
| 6 | +6 | Simon MURRAY (Ross County) |
| 4 | +4 | Kyle CONNELL (Cove Rangers) |
| +4 | Ruari PATON (Queen's Park) | |
| +4 | Blair HENDERSON (Spartans) | |
| +4 | Tiwi DARAMOLA (Kelty Hearts) | |
| 3 | +3 | Bruce ANDERSON (Livingston) |
| +3 | Paul McLEAN (Stirling Albion) | |
| +3 | Brian GRAHAM (Partick Thistle) | |
| +3 | Nathan AUSTIN (East Fife) | |
| +3 | Mikael MANDRON (St.Mirren) | |
| +3 | Robbie CRAWFORD (Morton) | |
| +3 | Zach ROBINSON (Dundee) | |
| +3 | Craig JOHNSTON (Kelty Hearts) | |
| +3 | Lewis McCANN (Dunfermline) | |
| +3 | Ross MacIVER (Falkirk) | |
| +3 | Fraser BRYDEN (Ayr United) | |
| +3 | Rumarn BURRELL (Cove Rangers) | |
| +3 | Gavin REILLY (Queen of the South) |