| 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 | Stirling Albion | 3 | 2 | 1 | 0 | 5 | 3 | +2 | 7 | WWX- | |
| 2 | 1 | Ayr United | 2 | 1 | 1 | 0 | 2 | 1 | +1 | 5 | WX-- | |
| 3 | 2 | St.Johnstone | 2 | 1 | 0 | 1 | 4 | 1 | +3 | 3 | WL-- | |
| 4 | 1 | Stenhousemuir | 3 | 1 | 0 | 2 | 2 | 3 | -1 | 3 | LLW- | |
| 5 | 1 | Alloa Athletic | 2 | 0 | 0 | 2 | 1 | 6 | -5 | 0 | LL-- | |
| Saturday, 22 July 2023 | |||||
| 3 | Stirling Albion | 2-1 | Stenhousemuir | ||
| 3 | Carrick | 45 | Yates | ||
| 24 | Dunsmore | ||||
| 3 | Alloa Athletic | 0-4 | St.Johnstone | ||
| 1 | Ballantyne | ||||
| 20 | McGowan | ||||
| 63 | May | ||||
| 89 | McCrystal | ||||
| Group B | Overall | |||||||||||
| P | W | D | L | F | A | Gdf | Pts | Form | ||||
| 1 | Partick Thistle | 3 | 1 | 2 | 0 | 5 | 4 | +1 | 6 | XWX- | ||
| 2 | Falkirk | 2 | 1 | 1 | 0 | 4 | 3 | +1 | 5 | XW-- | ||
| 3 | 2 | Dundee United | 3 | 1 | 0 | 2 | 4 | 3 | +1 | 3 | WLL- | |
| 4 | 1 | Spartans | 2 | 1 | 0 | 1 | 2 | 2 | +0 | 3 | LW-- | |
| 5 | 1 | Peterhead | 2 | 0 | 1 | 1 | 1 | 4 | -3 | 1 | LX-- | |
| Saturday, 22 July 2023 | |||||
| 3 | Dundee United | 3-0 | Peterhead | ||
| 22 | Moult | ||||
| 76(p) | Holt | ||||
| 79(p) | Holt | ||||
| 3 | Partick Thistle | 2-2 | Falkirk | ||
| 68 | Graham | 14 | MacIver | ||
| 90+3 | Lyon | 71 | Agyeman | ||
| Group C | Overall | |||||||||||
| P | W | D | L | F | A | Gdf | Pts | Form | ||||
| 1 | Hamilton | 3 | 2 | 1 | 0 | 5 | 2 | +3 | 8 | XWW- | ||
| 2 | Cove Rangers | 2 | 2 | 0 | 0 | 8 | 4 | +4 | 6 | WW-- | ||
| 3 | Livingston | 2 | 1 | 1 | 0 | 4 | 1 | +3 | 4 | XW-- | ||
| 4 | 1 | Clyde | 2 | 0 | 0 | 2 | 3 | 8 | -5 | 0 | LL-- | |
| 5 | 1 | Brechin City | 3 | 0 | 0 | 3 | 2 | 7 | -5 | 0 | LLL- | |
| Saturday, 22 July 2023 | |||||
| 3 | Livingston | 1-1 | Hamilton | ||
| 90 | Anderson | 31 | Winter | ||
| 3 | Brechin City | 2-3 | Cove Rangers | ||
| 30 | McGrath | 34 | Reynolds | ||
| 39(p) | Loudon | 74 | Connell | ||
| 81 | Connell | ||||
| Group D | Overall | |||||||||||
| P | W | D | L | F | A | Gdf | Pts | Form | ||||
| 1 | 1 | Ross County | 2 | 2 | 0 | 0 | 7 | 2 | +5 | 6 | WW-- | |
| 2 | 1 | Morton | 3 | 2 | 0 | 1 | 7 | 3 | +4 | 6 | LWW- | |
| 3 | Kelty Hearts | 2 | 1 | 0 | 1 | 6 | 6 | +0 | 3 | WL-- | ||
| 4 | 1 | Stranraer | 3 | 1 | 0 | 2 | 3 | 9 | -6 | 3 | WLL- | |
| 5 | 1 | Edinburgh City | 2 | 0 | 0 | 2 | 4 | 7 | -3 | 0 | LL-- | |
| Saturday, 22 July 2023 | |||||
| 3 | Stranraer | 2-1 | Edinburgh City | ||
| 38 | Armour | 49 | Shanley | ||
| 79(p) | Orr | ||||
| 3 | Ross County | 2-1 | Morton | ||
| 70 | Henderson | 37 | Oakley | ||
| 78 | Murray | ||||
| Group E | Overall | |||||||||||
| P | W | D | L | F | A | Gdf | Pts | Form | ||||
| 1 | Airdrieonians | 2 | 2 | 0 | 0 | 3 | 0 | +3 | 6 | WW-- | ||
| 2 | 2 | Dumbarton | 3 | 1 | 1 | 1 | 2 | 3 | -1 | 5 | OWL- | |
| 3 | Inverness CT | 2 | 1 | 0 | 1 | 3 | 3 | +0 | 3 | LW-- | ||
| 4 | 2 | Dundee | 2 | 1 | 0 | 1 | 1 | 1 | +0 | 3 | LW-- | |
| 5 | Bonnyrigg Rose | 3 | 0 | 1 | 2 | 1 | 3 | -2 | 1 | OLL- | ||
| Saturday, 22 July 2023 | |||||
| 3 | Airdrieonians | 1-0 | Dundee | ||
| 89(p) | McCabe | ||||
| 3 | Dumbarton | 0-0 | Bonnyrigg Rose | ||
| Group F | Overall | |||||||||||
| P | W | D | L | F | A | Gdf | Pts | Form | ||||
| 1 | 2 | Kilmarnock | 2 | 2 | 0 | 0 | 5 | 0 | +5 | 6 | WW-- | |
| 2 | 1 | Dunfermline | 3 | 1 | 1 | 1 | 5 | 3 | +2 | 5 | LWX- | |
| 3 | 1 | Raith Rovers | 2 | 1 | 1 | 0 | 3 | 1 | +2 | 4 | WX-- | |
| 4 | Albion Rovers | 1 | 0 | 0 | 1 | 0 | 2 | -2 | 0 | L--- | ||
| 5 | Annan Athletic | 2 | 0 | 0 | 2 | 0 | 7 | -7 | 0 | LL-- | ||
| Saturday, 22 July 2023 | |||||
| 3 | Dunfermline | 0-2 | Kilmarnock | ||
| 4 | Murray | ||||
| 81 | Vassell | ||||
| Group G | Overall | |||||||||||
| P | W | D | L | F | A | Gdf | Pts | Form | ||||
| 1 | Motherwell | 3 | 2 | 1 | 0 | 6 | 3 | +3 | 8 | WXW- | ||
| 2 | East Fife | 2 | 1 | 1 | 0 | 3 | 1 | +2 | 5 | WO-- | ||
| 3 | Queen of the South | 2 | 1 | 1 | 0 | 5 | 3 | +2 | 4 | WX-- | ||
| 4 | Queen's Park | 2 | 0 | 1 | 1 | 0 | 1 | -1 | 1 | LO-- | ||
| 5 | Elgin City | 3 | 0 | 0 | 3 | 1 | 7 | -6 | 0 | LLL- | ||
| Saturday, 22 July 2023 | |||||
| 3 | Motherwell | 1-0 | Queen's Park | ||
| 29 | Obika | ||||
| 3 | Elgin City | 0-2 | Queen of the South | ||
| 17 | McKechnie | ||||
| 89 | McKay | ||||
| Group H | Overall | |||||||||||
| P | W | D | L | F | A | Gdf | Pts | Form | ||||
| 1 | Forfar Athletic | 2 | 2 | 0 | 0 | 3 | 1 | +2 | 6 | WW-- | ||
| 2 | Montrose | 3 | 1 | 1 | 1 | 3 | 3 | +0 | 5 | XLW- | ||
| 3 | 2 | St.Mirren | 2 | 1 | 0 | 1 | 4 | 1 | +3 | 3 | WL-- | |
| 4 | Cowdenbeath | 3 | 0 | 2 | 1 | 2 | 3 | -1 | 2 | XXL- | ||
| 5 | 2 | Arbroath | 2 | 0 | 1 | 1 | 1 | 5 | -4 | 2 | LX-- | |
| Saturday, 22 July 2023 | |||||
| 3 | St.Mirren | 4-0 | Arbroath | ||
| 10 | Mandron | ||||
| 45 | O'Hara | ||||
| 71 | Nachmani | ||||
| 79 | Nachmani | ||||
| 3 | Cowdenbeath | 1-1 | Montrose | ||
| 72(p) | 60 | Webster | |||
| 4 | +2 | Kyle CONNELL (Cove Rangers) |
| +1 | Simon MURRAY (Ross County) | |
| 3 | Nathan AUSTIN (East Fife) | |
| Lewis McCANN (Dunfermline) | ||
| Tiwi DARAMOLA (Kelty Hearts) | ||
| 2 | +2 | Kevin HOLT (Dundee United) |
| +1 | Kieran McKECHNIE (Queen of the South) | |
| +1 | Brian GRAHAM (Partick Thistle) | |
| +1 | Jonathan OBIKA (Motherwell) | |
| Aaron DORAN (Inverness CT) | ||
| Robbie CRAWFORD (Morton) | ||
| +2 | Stav NACHMANI (St.Mirren) | |
| +1 | Dale CARRICK (Stirling Albion) | |
| Craig JOHNSTON (Kelty Hearts) | ||
| Harry MILNE (Partick Thistle) | ||
| Russell McLEAN (Edinburgh City) | ||
| +1 | Fraser MURRAY (Kilmarnock) | |
| +1 | Andy WINTER (Hamilton) | |
| Blair HENDERSON (Spartans) | ||
| Blair SPITTAL (Motherwell) | ||
| +1 | Ross MacIVER (Falkirk) | |
| Rumarn BURRELL (Cove Rangers) | ||
| Gavin REILLY (Queen of the South) |