| 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 | Hearts | 2 | 2 | 0 | 0 | 5 | 0 | +5 | 6 | WW-- | ||
| 2 | 1 | Stirling Albion | 2 | 1 | 1 | 0 | 5 | 4 | +1 | 5 | XW-- | |
| 3 | 1 | Inverness CT | 2 | 1 | 1 | 0 | 4 | 2 | +2 | 4 | XW-- | |
| 4 | 1 | Peterhead | 3 | 1 | 0 | 2 | 3 | 5 | -2 | 3 | WLL- | |
| 5 | 1 | Cove Rangers | 3 | 0 | 0 | 3 | 3 | 9 | -6 | 0 | LLL- | |
| Saturday, 17 July 2021 | |||||
| 3 | Inverness CT | 2-2 | Stirling Albion | ||
| 27 | MacGregor | 4 | Mackin | ||
| 49 | Sutherland | 20 | Moore | ||
| 3 | Peterhead | 3-1 | Cove Rangers | ||
| 3 | Brown | 12 | Megginson | ||
| 44 | Cameron | ||||
| 54 | McLean | ||||
| Group B | Overall | |||||||||||
| P | W | D | L | F | A | Gdf | Pts | Form | ||||
| 1 | Dundee United | 3 | 3 | 0 | 0 | 8 | 1 | +7 | 9 | WWW- | ||
| 2 | Arbroath | 3 | 2 | 0 | 1 | 3 | 1 | +2 | 6 | LWW- | ||
| 3 | Kelty Hearts | 2 | 1 | 0 | 1 | 3 | 1 | +2 | 3 | WL-- | ||
| 4 | East Fife | 2 | 0 | 0 | 2 | 0 | 5 | -5 | 0 | LL-- | ||
| 5 | Elgin City | 2 | 0 | 0 | 2 | 1 | 7 | -6 | 0 | LL-- | ||
| Saturday, 17 July 2021 | |||||
| 3 | Dundee United | 1-0 | Arbroath | ||
| 21 | Mulgrew | ||||
| 3 | Kelty Hearts | 3-0 | East Fife | ||
| 13 | Austin | ||||
| 25 | Austin | ||||
| 87 | Agyeman | ||||
| Group C | Overall | |||||||||||
| P | W | D | L | F | A | Gdf | Pts | Form | ||||
| 1 | Forfar Athletic | 3 | 2 | 1 | 0 | 4 | 0 | +4 | 8 | WOW- | ||
| 2 | 1 | Dundee | 2 | 2 | 0 | 0 | 7 | 0 | +7 | 6 | WW-- | |
| 3 | 1 | Montrose | 2 | 1 | 1 | 0 | 3 | 0 | +3 | 4 | OW-- | |
| 4 | Ross County | 2 | 0 | 0 | 2 | 0 | 6 | -6 | 0 | LL-- | ||
| 5 | Brora Rangers | 3 | 0 | 0 | 3 | 0 | 8 | -8 | 0 | LLL- | ||
| Saturday, 17 July 2021 | |||||
| 3 | Brora Rangers | 0-1 | Forfar Athletic | ||
| 80 | Gallagher | ||||
| 3 | Ross County | 0-3 | Dundee | ||
| Score awarded as 0-3. | |||||
| Group D | Overall | |||||||||||
| P | W | D | L | F | A | Gdf | Pts | Form | ||||
| 1 | Raith Rovers | 2 | 2 | 0 | 0 | 5 | 0 | +5 | 6 | WW-- | ||
| 2 | 1 | Cowdenbeath | 3 | 2 | 0 | 1 | 4 | 3 | +1 | 6 | WWL- | |
| 3 | 1 | Livingston | 2 | 1 | 0 | 1 | 4 | 2 | +2 | 3 | LW-- | |
| 4 | Alloa Athletic | 2 | 1 | 0 | 1 | 2 | 2 | +0 | 3 | WL-- | ||
| 5 | Brechin City | 3 | 0 | 0 | 3 | 2 | 10 | -8 | 0 | LLL- | ||
| Saturday, 17 July 2021 | |||||
| 3 | Cowdenbeath | 3-2 | Brechin City | ||
| 26 | Renton | 67 | Wood | ||
| 28(p) | Buchanan | 77(p) | Inglis | ||
| 89 | Renton | ||||
| 3 | Alloa Athletic | 2-1 | Livingston | ||
| 82 | Taggart | 63 | Anderson | ||
| 86(p) | Trouten | ||||
| Group E | Overall | |||||||||||
| P | W | D | L | F | A | Gdf | Pts | Form | ||||
| 1 | 2 | Hamilton | 2 | 2 | 0 | 0 | 3 | 1 | +2 | 6 | WW-- | |
| 2 | 1 | Ayr United | 2 | 1 | 1 | 0 | 3 | 0 | +3 | 4 | WO-- | |
| 3 | 1 | Albion Rovers | 3 | 0 | 2 | 1 | 2 | 6 | -4 | 4 | XLO- | |
| 4 | 2 | Falkirk | 2 | 1 | 0 | 1 | 6 | 3 | +3 | 3 | LW-- | |
| 5 | FC Edinburgh | 3 | 0 | 1 | 2 | 1 | 5 | -4 | 1 | XLL- | ||
| Saturday, 17 July 2021 | |||||
| 3 | Falkirk | 1-2 | Hamilton | ||
| 46 | Nesbitt | 79(p) | Hughes | ||
| 87 | Hamilton | ||||
| 3 | Albion Rovers | 1-1 | FC Edinburgh | ||
| 4 | Byrne | 70 | Hilton | ||
| Group F | Overall | |||||||||||
| P | W | D | L | F | A | Gdf | Pts | Form | ||||
| 1 | 1 | Motherwell | 2 | 2 | 0 | 0 | 4 | 2 | +2 | 6 | WW-- | |
| 2 | 1 | Queen's Park | 3 | 1 | 1 | 1 | 1 | 1 | +0 | 4 | OLW- | |
| 3 | 2 | Queen of the South | 3 | 1 | 0 | 2 | 5 | 5 | +0 | 3 | LWL- | |
| 4 | 1 | Airdrieonians | 2 | 0 | 2 | 0 | 1 | 1 | +0 | 3 | OX-- | |
| 5 | 1 | Annan Athletic | 2 | 0 | 1 | 1 | 2 | 4 | -2 | 2 | LX-- | |
| Saturday, 17 July 2021 | |||||
| 3 | Motherwell | 3-2 | Queen of the South | ||
| 49 | Watt | 40 | Paton | ||
| 72 | Lamie | 45 | Paton | ||
| 75 | Woolery | ||||
| 3 | Queen's Park | 0-0 | Airdrieonians | ||
| Group G | Overall | |||||||||||
| P | W | D | L | F | A | Gdf | Pts | Form | ||||
| 1 | Stranraer | 3 | 2 | 0 | 1 | 4 | 1 | +3 | 6 | WLW- | ||
| 2 | Kilmarnock | 2 | 2 | 0 | 0 | 4 | 1 | +3 | 6 | WW-- | ||
| 3 | Clyde | 2 | 1 | 0 | 1 | 2 | 2 | +0 | 3 | LW-- | ||
| 4 | Morton | 2 | 0 | 1 | 1 | 0 | 3 | -3 | 2 | OL-- | ||
| 5 | East Kilbride | 3 | 0 | 1 | 2 | 0 | 3 | -3 | 1 | LOL- | ||
| Saturday, 17 July 2021 | |||||
| 3 | Clyde | 1-2 | Kilmarnock | ||
| 57(p) | Love | 1 | Alston | ||
| 19(p) | Cameron | ||||
| 3 | Stranraer | 1-0 | East Kilbride | ||
| 26 | Yates | ||||
| Group H | Overall | |||||||||||
| P | W | D | L | F | A | Gdf | Pts | Form | ||||
| 1 | 1 | Dunfermline | 3 | 2 | 0 | 1 | 9 | 4 | +5 | 6 | WLW- | |
| 2 | 1 | St.Mirren | 2 | 2 | 0 | 0 | 4 | 0 | +4 | 6 | WW-- | |
| 3 | Stenhousemuir | 2 | 1 | 0 | 1 | 3 | 3 | +0 | 3 | LW-- | ||
| 4 | Partick Thistle | 2 | 1 | 0 | 1 | 4 | 5 | -1 | 3 | WL-- | ||
| 5 | Dumbarton | 3 | 0 | 0 | 3 | 2 | 10 | -8 | 0 | LLL- | ||
| Saturday, 17 July 2021 | |||||
| 3 | Dunfermline | 5-1 | Dumbarton | ||
| 2 | Todorov | 56 | MacLean | ||
| 4 | Thomas | ||||
| 29 | Wighton | ||||
| 51(og) | Buchanan | ||||
| 71 | O'Hara | ||||
| 3 | Stenhousemuir | 1-2 | Partick Thistle | ||
| 32(p) | Orr | 52 | Rudden | ||
| 73 | Graham | ||||
| 3 | +1 | Nikolay TODOROV (Dunfermline) |
| Lawrence SHANKLAND (Dundee United) | ||
| +2 | Ruari PATON (Queen of the South) | |
| 2 | Lewis VAUGHAN (Raith Rovers) | |
| +1 | Ross MacLEAN (Dumbarton) | |
| Brad SPENCER (Raith Rovers) | ||
| Nathan FLANAGAN (Stirling Albion) | ||
| Gary MACKAY-STEVEN (Hearts) | ||
| +1 | Zak RUDDEN (Partick Thistle) | |
| +2 | Kris RENTON (Cowdenbeath) | |
| +2 | Nathan AUSTIN (Kelty Hearts) | |
| Alistair ROY (Queen of the South) | ||
| +1 | Brian GRAHAM (Partick Thistle) | |
| +1 | Liam BUCHANAN (Cowdenbeath, 1p) | |
| Callumn MORRISON (Falkirk) | ||
| Tomi ADELOYE (Ayr United) | ||
| Paul McMULLAN (Dundee) | ||
| Fraser FYVIE (Cove Rangers) | ||
| Luke DONNELLY (Arbroath) | ||
| Liam BOYCE (Hearts) |