| 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 | Dundee United | 2 | 1 | 1 | 0 | 3 | 2 | +1 | 5 | WX-- | |
| 2 | 1 | Hearts | 2 | 1 | 1 | 0 | 3 | 1 | +2 | 4 | WX-- | |
| 3 | 2 | Cowdenbeath | 2 | 1 | 0 | 1 | 2 | 2 | +0 | 3 | LW-- | |
| 4 | Stenhousemuir | 1 | 0 | 0 | 1 | 1 | 2 | -1 | 0 | L--- | ||
| 5 | East Fife | 1 | 0 | 0 | 1 | 0 | 2 | -2 | 0 | L--- | ||
| Tuesday, 16 July 2019 | |||||
| 2 | Cowdenbeath | 0-2 | Hearts | ||
| 8 | Halkett | ||||
| 22 | McDonald | ||||
| 2 | Stenhousemuir | 1-2 | Dundee United | ||
| 70 | Munro | 51 | Watson | ||
| 54 | Butcher | ||||
| Group B | Overall | |||||||||||
| P | W | D | L | F | A | Gdf | Pts | Form | ||||
| 1 | Ross County | 2 | 2 | 0 | 0 | 8 | 1 | +7 | 6 | WW-- | ||
| 2 | Forfar Athletic | 1 | 1 | 0 | 0 | 3 | 0 | +3 | 3 | W--- | ||
| 3 | 1 | Montrose | 2 | 1 | 0 | 1 | 2 | 4 | -2 | 3 | WL-- | |
| 4 | 1 | St.Johnstone | 1 | 0 | 0 | 1 | 0 | 1 | -1 | 0 | L--- | |
| 5 | Brechin City | 2 | 0 | 0 | 2 | 0 | 7 | -7 | 0 | LL-- | ||
| Tuesday, 16 July 2019 | |||||
| 2 | Brechin City | 0-4 | Ross County | ||
| 33 | Stewart | ||||
| 44 | Stewart | ||||
| 49 | McKay | ||||
| 75 | Spittal | ||||
| 2 | Montrose | 1-0 | St.Johnstone | ||
| 72 | Masson | ||||
| Group C | Overall | |||||||||||
| P | W | D | L | F | A | Gdf | Pts | Form | ||||
| 1 | Arbroath | 2 | 2 | 0 | 0 | 8 | 2 | +6 | 6 | WW-- | ||
| 2 | Hibernian | 1 | 0 | 1 | 0 | 1 | 1 | +0 | 2 | X--- | ||
| 3 | 2 | Elgin City | 2 | 0 | 1 | 1 | 4 | 5 | -1 | 2 | XL-- | |
| 4 | Alloa Athletic | 1 | 0 | 1 | 0 | 3 | 3 | +0 | 1 | X--- | ||
| 5 | 2 | Stirling Albion | 2 | 0 | 1 | 1 | 2 | 7 | -5 | 1 | LX-- | |
| Tuesday, 16 July 2019 | |||||
| 2 | Alloa Athletic | 3-3 | Elgin City | ||
| 54 | Trouten | 30 | Dingwall | ||
| 57 | Buchanan | 55 | Sutherland | ||
| 75 | Cawley | 88 | Bronsky | ||
| Wednesday, 17 July 2019 | |||||
| 2 | Stirling Albion | 1-6 | Arbroath | ||
| 47 | Mackin | 1 | Gold | ||
| 28 | McKenna | ||||
| 57 | Gold | ||||
| 82 | Hamilton | ||||
| 87 | Spence | ||||
| 90 | Spence | ||||
| Group D | Overall | |||||||||||
| P | W | D | L | F | A | Gdf | Pts | Form | ||||
| 1 | Dundee | 2 | 1 | 1 | 0 | 3 | 0 | +3 | 5 | OW-- | ||
| 2 | Peterhead | 2 | 1 | 1 | 0 | 2 | 1 | +1 | 5 | OW-- | ||
| 3 | Inverness CT | 1 | 0 | 1 | 0 | 0 | 0 | +0 | 1 | O--- | ||
| 4 | Cove Rangers | 2 | 0 | 1 | 1 | 1 | 2 | -1 | 1 | OL-- | ||
| 5 | Raith Rovers | 1 | 0 | 0 | 1 | 0 | 3 | -3 | 0 | L--- | ||
| Tuesday, 16 July 2019 | |||||
| 2 | Peterhead | 0-0 | Inverness CT | ||
| Wednesday, 17 July 2019 | |||||
| 2 | Cove Rangers | 0-0 | Dundee | ||
| Group E | Overall | |||||||||||
| P | W | D | L | F | A | Gdf | Pts | Form | ||||
| 1 | 2 | Morton | 1 | 1 | 0 | 0 | 6 | 1 | +5 | 3 | W--- | |
| 2 | 1 | Motherwell | 1 | 1 | 0 | 0 | 3 | 0 | +3 | 3 | W--- | |
| 3 | 1 | Dumbarton | 2 | 1 | 0 | 1 | 2 | 6 | -4 | 3 | LW-- | |
| 4 | 1 | Queen of the South | 2 | 0 | 1 | 1 | 3 | 6 | -3 | 2 | XL-- | |
| 5 | 1 | Annan Athletic | 2 | 0 | 1 | 1 | 3 | 4 | -1 | 1 | XL-- | |
| Tuesday, 16 July 2019 | |||||
| 2 | Morton | 6-1 | Dumbarton | ||
| 15(og) | Neill | 63 | Neill | ||
| 17 | Grant | ||||
| 23 | Jacobs | ||||
| 31 | Strapp | ||||
| 45 | Sutton | ||||
| 69 | McHugh | ||||
| 2 | Queen of the South | 3-3 | Annan Athletic | ||
| 23 | Murray | 34 | Douglas | ||
| 26 | Mercer | 54 | McLear | ||
| 42 | Dobbie | 81 | Wooding-Holt | ||
| Group F | Overall | |||||||||||
| P | W | D | L | F | A | Gdf | Pts | Form | ||||
| 1 | Partick Thistle | 2 | 2 | 0 | 0 | 3 | 1 | +2 | 6 | WW-- | ||
| 2 | 1 | Hamilton | 2 | 1 | 1 | 0 | 3 | 1 | +2 | 4 | WO-- | |
| 3 | 1 | Queen's Park | 2 | 0 | 1 | 1 | 1 | 2 | -1 | 2 | LO-- | |
| 4 | 1 | Airdrieonians | 1 | 0 | 0 | 1 | 0 | 1 | -1 | 0 | L--- | |
| 5 | 1 | Clyde | 1 | 0 | 0 | 1 | 1 | 3 | -2 | 0 | L--- | |
| Tuesday, 16 July 2019 | |||||
| 2 | Queen's Park | 1-2 | Partick Thistle | ||
| 56 | Kouider-Aissa | 6 | Miller | ||
| 36 | Robson | ||||
| Wednesday, 17 July 2019 | |||||
| 2 | Clyde | 1-3 | Hamilton | ||
| 57 | Syvertsen | 31 | McMann | ||
| 50 | Alston | ||||
| 76 | Smith | ||||
| Group G | Overall | |||||||||||
| P | W | D | L | F | A | Gdf | Pts | Form | ||||
| 1 | 1 | Livingston | 2 | 1 | 1 | 0 | 3 | 2 | +1 | 5 | WX-- | |
| 2 | 1 | Falkirk | 2 | 1 | 1 | 0 | 2 | 1 | +1 | 4 | WX-- | |
| 3 | 2 | Ayr United | 2 | 1 | 0 | 1 | 8 | 2 | +6 | 3 | LW-- | |
| 4 | Stranraer | 1 | 0 | 0 | 1 | 0 | 1 | -1 | 0 | L--- | ||
| 5 | Berwick Rangers | 1 | 0 | 0 | 1 | 0 | 7 | -7 | 0 | L--- | ||
| Tuesday, 16 July 2019 | |||||
| 2 | Falkirk | 1-0 | Stranraer | ||
| 9 | McManus | ||||
| 2 | Livingston | 2-1 | Ayr United | ||
| 25 | Souda | 51 | Murdoch | ||
| 83 | Lamie | ||||
| Group H | Overall | |||||||||||
| P | W | D | L | F | A | Gdf | Pts | Form | ||||
| 1 | Dunfermline | 2 | 2 | 0 | 0 | 9 | 2 | +7 | 6 | WW-- | ||
| 2 | 2 | St.Mirren | 2 | 1 | 0 | 1 | 3 | 3 | +0 | 3 | WL-- | |
| 3 | 1 | Albion Rovers | 2 | 1 | 0 | 1 | 1 | 6 | -5 | 3 | LW-- | |
| 4 | 1 | East Kilbride | 1 | 0 | 0 | 1 | 0 | 1 | -1 | 0 | L--- | |
| 5 | 2 | FC Edinburgh | 1 | 0 | 0 | 1 | 0 | 1 | -1 | 0 | L--- | |
| Wednesday, 17 July 2019 | |||||
| 2 | Dunfermline | 6-0 | Albion Rovers | ||
| 2 | Turner | ||||
| 19 | Nisbet | ||||
| 25 | Nisbet | ||||
| 40 | Comrie | ||||
| 45 | Nisbet | ||||
| 53 | Turner | ||||
| 2 | St.Mirren | 1-0 | FC Edinburgh | ||
| 88(p) | Djorkaeff | ||||
| 4 | +2 | Ross STEWART (Ross County) |
| 3 | +3 | Kevin NISBET (Dunfermline) |
| 2 | Kris DOOLAN (Ayr United) | |
| +2 | Kyle TURNER (Dunfermline) | |
| +2 | David GOLD (Arbroath) | |
| +1 | Shane SUTHERLAND (Elgin City) | |
| Andrew NELSON (Dundee, 1p) | ||
| Luke McCOWAN (Ayr United) | ||
| +2 | Greig SPENCE (Arbroath) | |
| Michael MOFFAT (Ayr United) | ||
| +1 | Billy McKAY (Ross County) |