| 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 | 3 | 2 | 1 | 0 | 4 | 2 | +2 | 8 | WWX- | |
| 2 | 1 | Stirling Albion | 3 | 2 | 1 | 0 | 5 | 3 | +2 | 7 | WWX- | |
| 3 | St.Johnstone | 3 | 1 | 0 | 2 | 5 | 3 | +2 | 3 | LWL- | ||
| 4 | 1 | Alloa Athletic | 3 | 1 | 0 | 2 | 4 | 7 | -3 | 3 | WLL- | |
| 5 | 1 | Stenhousemuir | 4 | 1 | 0 | 3 | 3 | 6 | -3 | 3 | LLLW | |
| Tuesday, 25 July 2023 | |||||
| 4 | St.Johnstone | 1-2 | Ayr United | ||
| 43 | Kucheriavyi | 29 | Stanger | ||
| 71 | Dempsey | ||||
| 4 | Stenhousemuir | 1-3 | Alloa Athletic | ||
| 29 | Brown | 37 | Buchanan | ||
| 72 | Sammon | ||||
| 79 | Neill | ||||
| Group B | Overall | |||||||||||
| P | W | D | L | F | A | Gdf | Pts | Form | ||||
| 1 | 2 | Dundee United | 4 | 2 | 0 | 2 | 5 | 3 | +2 | 6 | WWLL | |
| 2 | 1 | Partick Thistle | 3 | 1 | 2 | 0 | 5 | 4 | +1 | 6 | XWX- | |
| 3 | 1 | Spartans | 3 | 2 | 0 | 1 | 4 | 3 | +1 | 6 | WLW- | |
| 4 | 2 | Falkirk | 3 | 1 | 1 | 1 | 4 | 4 | +0 | 5 | LXW- | |
| 5 | Peterhead | 3 | 0 | 1 | 2 | 2 | 6 | -4 | 1 | LLX- | ||
| Tuesday, 25 July 2023 | |||||
| 4 | Falkirk | 0-1 | Dundee United | ||
| 28 | Fotheringham | ||||
| Wednesday, 26 July 2023 | |||||
| 4 | Peterhead | 1-2 | Spartans | ||
| 50 | Shanks | 9 | Henderson | ||
| 55 | Russell | ||||
| Group C | Overall | |||||||||||
| P | W | D | L | F | A | Gdf | Pts | Form | ||||
| 1 | Hamilton | 3 | 2 | 1 | 0 | 5 | 2 | +3 | 8 | XWW- | ||
| 2 | 1 | Livingston | 3 | 2 | 1 | 0 | 9 | 1 | +8 | 7 | WXW- | |
| 3 | 1 | Cove Rangers | 3 | 2 | 0 | 1 | 8 | 9 | -1 | 6 | LWW- | |
| 4 | 1 | Brechin City | 4 | 1 | 0 | 3 | 4 | 8 | -4 | 3 | WLLL | |
| 5 | 1 | Clyde | 3 | 0 | 0 | 3 | 4 | 10 | -6 | 0 | LLL- | |
| Tuesday, 25 July 2023 | |||||
| 4 | Clyde | 1-2 | Brechin City | ||
| 50 | Cameron | 45+1 | Loudon | ||
| 48 | McGrath | ||||
| 4 | Cove Rangers | 0-5 | Livingston | ||
| 44 | Parkes | ||||
| 55 | Obileye | ||||
| 59 | Anderson | ||||
| 81 | Kelly | ||||
| 90+2 | Kelly | ||||
| Group D | Overall | |||||||||||
| P | W | D | L | F | A | Gdf | Pts | Form | ||||
| 1 | Ross County | 3 | 3 | 0 | 0 | 10 | 3 | +7 | 9 | WWW- | ||
| 2 | Morton | 3 | 2 | 0 | 1 | 7 | 3 | +4 | 6 | LWW- | ||
| 3 | Kelty Hearts | 3 | 2 | 0 | 1 | 8 | 6 | +2 | 6 | WWL- | ||
| 4 | Stranraer | 4 | 1 | 0 | 3 | 3 | 11 | -8 | 3 | LWLL | ||
| 5 | Edinburgh City | 3 | 0 | 0 | 3 | 5 | 10 | -5 | 0 | LLL- | ||
| Tuesday, 25 July 2023 | |||||
| 4 | Kelty Hearts | 2-0 | Stranraer | ||
| 5 | Daramola | ||||
| 65 | Johnston | ||||
| Wednesday, 26 July 2023 | |||||
| 4 | Edinburgh City | 1-3 | Ross County | ||
| 51 | Shanley | 20 | Randall | ||
| 48 | Murray | ||||
| 59 | White | ||||
| Group E | Overall | |||||||||||
| P | W | D | L | F | A | Gdf | Pts | Form | ||||
| 1 | Airdrieonians | 3 | 3 | 0 | 0 | 6 | 2 | +4 | 9 | WWW- | ||
| 2 | 2 | Dundee | 3 | 2 | 0 | 1 | 4 | 2 | +2 | 6 | WLW- | |
| 3 | 1 | Dumbarton | 4 | 1 | 1 | 2 | 3 | 6 | -3 | 5 | LOWL | |
| 4 | 1 | Inverness CT | 3 | 1 | 0 | 2 | 5 | 6 | -1 | 3 | LLW- | |
| 5 | Bonnyrigg Rose | 3 | 0 | 1 | 2 | 1 | 3 | -2 | 1 | OLL- | ||
| Tuesday, 25 July 2023 | |||||
| 4 | Inverness CT | 2-3 | Airdrieonians | ||
| 62 | Gilmour | 22 | Ballantyne | ||
| 78(p) | McKay | 29 | Telfer | ||
| 88 | Todorov | ||||
| Wednesday, 26 July 2023 | |||||
| 4 | Dundee | 3-1 | Dumbarton | ||
| 38 | Robinson | 41 | Wallace | ||
| 44 | Pineda | ||||
| 77(p) | Robinson | ||||
| Group F | Overall | |||||||||||
| P | W | D | L | F | A | Gdf | Pts | Form | ||||
| 1 | 1 | Dunfermline | 4 | 2 | 1 | 1 | 8 | 3 | +5 | 8 | WLWX | |
| 2 | 1 | Kilmarnock | 3 | 2 | 1 | 0 | 7 | 2 | +5 | 7 | XWW- | |
| 3 | Raith Rovers | 3 | 1 | 2 | 0 | 5 | 3 | +2 | 6 | XWX- | ||
| 4 | Albion Rovers | 3 | 1 | 0 | 2 | 2 | 6 | -4 | 3 | LWL- | ||
| 5 | Annan Athletic | 3 | 0 | 0 | 3 | 1 | 9 | -8 | 0 | LLL- | ||
| Saturday, 22 July 2023 | |||||
| 4 | Annan Athletic | 1-2 | Albion Rovers | ||
| 43 | Goss | 77 | Prince | ||
| 82 | Joseph | ||||
| Tuesday, 25 July 2023 | |||||
| 4 | Albion Rovers | 0-3 | Dunfermline | ||
| 23 | Edwards | ||||
| 80 | Wighton | ||||
| 88 | Sutherland | ||||
| Wednesday, 26 July 2023 | |||||
| 4 | Kilmarnock | 2-2 | Raith Rovers | ||
| 42 | Cameron | 46 | Easton | ||
| 80 | Findlay | 74 | Dick | ||
| 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 | 3 | 1 | 2 | 0 | 3 | 1 | +2 | 7 | OWO- | ||
| 3 | Queen of the South | 3 | 1 | 2 | 0 | 5 | 3 | +2 | 5 | OWX- | ||
| 4 | Queen's Park | 3 | 1 | 1 | 1 | 5 | 1 | +4 | 4 | WLO- | ||
| 5 | Elgin City | 4 | 0 | 0 | 4 | 1 | 12 | -11 | 0 | LLLL | ||
| Tuesday, 25 July 2023 | |||||
| 4 | Queen's Park | 5-0 | Elgin City | ||
| 7 | Paton | ||||
| 33 | Paton | ||||
| 53 | Paton | ||||
| 66 | Paton | ||||
| 80 | Fox | ||||
| 4 | Queen of the South | 0-0 | East Fife | ||
| Group H | Overall | |||||||||||
| P | W | D | L | F | A | Gdf | Pts | Form | ||||
| 1 | Forfar Athletic | 3 | 3 | 0 | 0 | 6 | 2 | +4 | 9 | WWW- | ||
| 2 | 1 | St.Mirren | 3 | 2 | 0 | 1 | 5 | 1 | +4 | 6 | WWL- | |
| 3 | 1 | Montrose | 3 | 1 | 1 | 1 | 3 | 3 | +0 | 5 | XLW- | |
| 4 | Cowdenbeath | 4 | 0 | 2 | 2 | 2 | 4 | -2 | 2 | LXXL | ||
| 5 | Arbroath | 3 | 0 | 1 | 2 | 2 | 8 | -6 | 2 | LLX- | ||
| Tuesday, 25 July 2023 | |||||
| 4 | Cowdenbeath | 0-1 | St.Mirren | ||
| 90+4 | Olusanya | ||||
| 4 | Forfar Athletic | 3-1 | Arbroath | ||
| 10 | Morrison | 41 | Bird | ||
| 61 | Nditi | ||||
| 86 | Skelly | ||||
| 5 | +1 | Simon MURRAY (Ross County) |
| 4 | Kyle CONNELL (Cove Rangers) | |
| +4 | Ruari PATON (Queen's Park) | |
| +1 | Tiwi DARAMOLA (Kelty Hearts) | |
| 3 | Nathan AUSTIN (East Fife) | |
| +1 | Craig JOHNSTON (Kelty Hearts) | |
| +1 | Blair HENDERSON (Spartans) | |
| Lewis McCANN (Dunfermline) |