| 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 | 1 | Stenhousemuir | 4 | 1 | 0 | 3 | 3 | 6 | -3 | 3 | LLLW | |
| 5 | 1 | Alloa Athletic | 4 | 1 | 0 | 3 | 4 | 13 | -9 | 3 | LWLL | |
| Saturday, 29 July 2023 | |||||
| 5 | St.Johnstone | 0-4 | Stirling Albion | ||
| 11 | Spence | ||||
| 36 | Milne | ||||
| 48 | McLean | ||||
| 54 | McLean | ||||
| 5 | Ayr United | 6-0 | Alloa Athletic | ||
| 14 | Bryden | ||||
| 37 | McAllister | ||||
| 45+1 | Murphy | ||||
| 62 | Bryden | ||||
| 70 | Pendlebury | ||||
| 84 | Rose | ||||
| Group B | Overall | |||||||||||
| P | W | D | L | F | A | Gdf | Pts | Form | ||||
| 1 | 1 | Partick Thistle | 4 | 2 | 2 | 0 | 7 | 5 | +2 | 9 | WXWX | |
| 2 | 2 | Falkirk | 4 | 2 | 1 | 1 | 8 | 5 | +3 | 8 | WLXW | |
| 3 | 2 | Dundee United | 4 | 2 | 0 | 2 | 5 | 3 | +2 | 6 | WWLL | |
| 4 | 1 | Spartans | 4 | 2 | 0 | 2 | 5 | 5 | +0 | 6 | LWLW | |
| 5 | Peterhead | 4 | 0 | 1 | 3 | 3 | 10 | -7 | 1 | LLLX | ||
| Saturday, 29 July 2023 | |||||
| 5 | Falkirk | 4-1 | Peterhead | ||
| 29 | Lang | 6 | O'Keefe | ||
| 45+2 | MacIver | ||||
| 47 | Agyeman | ||||
| 56 | Miller | ||||
| 5 | Partick Thistle | 2-1 | Spartans | ||
| 52 | Lyon | 81 | Henderson | ||
| 88(p) | Graham | ||||
| Group C | Overall | |||||||||||
| P | W | D | L | F | A | Gdf | Pts | Form | ||||
| 1 | 1 | Livingston | 4 | 3 | 1 | 0 | 10 | 1 | +9 | 10 | WWXW | |
| 2 | 1 | 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, 29 July 2023 | |||||
| 5 | Hamilton | 2-2 | Cove Rangers | ||
| 13 | O'Hara | 44 | Gallagher | ||
| 90+6 | Tumilty | 60 | Burrell | ||
| 5 | Livingston | 1-0 | Clyde | ||
| 75 | Anderson | ||||
| 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, 29 July 2023 | |||||
| 5 | Morton | 4-1 | Edinburgh City | ||
| 33 | Broadfoot | 83 | Murray | ||
| 67 | Crawford | ||||
| 75 | King | ||||
| 88 | Blues | ||||
| 5 | Ross County | 3-3 | Kelty Hearts | ||
| 13 | Sims | 33 | McCluskey | ||
| 29 | Murray | 57 | Bia-Bi | ||
| 86 | Brown | 90+3(p) | Cunningham | ||
| 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, 29 July 2023 | |||||
| 5 | Bonnyrigg Rose | 0-1 | Airdrieonians | ||
| 73(p) | O'Connor | ||||
| Sunday, 30 July 2023 | |||||
| 5 | Dundee | 1-0 | Inverness CT | ||
| 60 | Robinson | ||||
| Group F | Overall | |||||||||||
| P | W | D | L | F | A | Gdf | Pts | Form | ||||
| 1 | 1 | Kilmarnock | 4 | 3 | 1 | 0 | 9 | 3 | +6 | 10 | WXWW | |
| 2 | 1 | Raith Rovers | 4 | 2 | 2 | 0 | 8 | 5 | +3 | 9 | WXWX | |
| 3 | 2 | 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, 29 July 2023 | |||||
| 5 | Albion Rovers | 1-2 | Kilmarnock | ||
| 62 | Joseph | 7 | Findlay | ||
| 41 | Watkins | ||||
| 5 | Annan Athletic | 2-3 | Raith Rovers | ||
| 27 | Galloway | 11 | Watson | ||
| 37 | Luissint | 51 | Smith | ||
| 79(p) | Vaughan | ||||
| Group G | Overall | |||||||||||
| P | W | D | L | F | A | Gdf | Pts | Form | ||||
| 1 | Motherwell | 4 | 3 | 1 | 0 | 9 | 3 | +6 | 11 | WWXW | ||
| 2 | 1 | Queen of the South | 4 | 2 | 2 | 0 | 7 | 4 | +3 | 8 | WOWX | |
| 3 | 1 | 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, 29 July 2023 | |||||
| 5 | Motherwell | 3-0 | East Fife | ||
| 32 | Miller | ||||
| 36 | Wilkinson | ||||
| 66 | Slattery | ||||
| 5 | Queen's Park | 1-2 | Queen of the South | ||
| 89 | Healy | 65 | Reilly | ||
| 77 | Cochrane | ||||
| Group H | Overall | |||||||||||
| P | W | D | L | F | A | Gdf | Pts | Form | ||||
| 1 | 1 | St.Mirren | 4 | 3 | 0 | 1 | 9 | 1 | +8 | 9 | WWWL | |
| 2 | 1 | Forfar Athletic | 4 | 3 | 0 | 1 | 6 | 6 | +0 | 9 | LWWW | |
| 3 | 2 | Arbroath | 4 | 1 | 1 | 2 | 5 | 8 | -3 | 5 | WLLX | |
| 4 | 1 | Montrose | 4 | 1 | 1 | 2 | 3 | 6 | -3 | 5 | LXLW | |
| 5 | 1 | Cowdenbeath | 4 | 0 | 2 | 2 | 2 | 4 | -2 | 2 | LXXL | |
| Saturday, 29 July 2023 | |||||
| 5 | St.Mirren | 4-0 | Forfar Athletic | ||
| 14 | Mandron | ||||
| 19 | Mandron | ||||
| 42(p) | O'Hara | ||||
| 45+1 | Gogic | ||||
| 5 | Arbroath | 3-0 | Montrose | ||
| 12 | McIntosh | ||||
| 70 | Dünnwald | ||||
| 79 | Bird | ||||
| 6 | +1 | Simon MURRAY (Ross County) |
| 4 | Kyle CONNELL (Cove Rangers) | |
| Ruari PATON (Queen's Park) | ||
| +1 | Blair HENDERSON (Spartans) | |
| Tiwi DARAMOLA (Kelty Hearts) | ||
| 3 | +1 | Bruce ANDERSON (Livingston) |
| +2 | Paul McLEAN (Stirling Albion) | |
| +1 | Brian GRAHAM (Partick Thistle) | |
| Nathan AUSTIN (East Fife) | ||
| +2 | Mikael MANDRON (St.Mirren) | |
| +1 | Robbie CRAWFORD (Morton) | |
| +1 | Zach ROBINSON (Dundee) | |
| Craig JOHNSTON (Kelty Hearts) | ||
| Lewis McCANN (Dunfermline) | ||
| +1 | Ross MacIVER (Falkirk) | |
| +2 | Fraser BRYDEN (Ayr United) | |
| +1 | Rumarn BURRELL (Cove Rangers) | |
| +1 | Gavin REILLY (Queen of the South) |