| 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 | Dundee United | 3 | 2 | 1 | 0 | 6 | 2 | +4 | 8 | WWX- | ||
| 2 | Hearts | 2 | 1 | 1 | 0 | 3 | 1 | +2 | 4 | WX-- | ||
| 3 | 2 | East Fife | 2 | 1 | 0 | 1 | 2 | 2 | +0 | 3 | WL-- | |
| 4 | 1 | Cowdenbeath | 3 | 1 | 0 | 2 | 2 | 5 | -3 | 3 | LLW- | |
| 5 | 1 | Stenhousemuir | 2 | 0 | 0 | 2 | 1 | 4 | -3 | 0 | LL-- | |
| Friday, 19 July 2019 | |||||
| 3 | Dundee United | 3-0 | Cowdenbeath | ||
| 26 | Sporle | ||||
| 59 | Shankland | ||||
| 86 | Appéré | ||||
| Saturday, 20 July 2019 | |||||
| 3 | East Fife | 2-0 | Stenhousemuir | ||
| 56 | Agnew | ||||
| 86(p) | Agnew | ||||
| Group B | Overall | |||||||||||
| P | W | D | L | F | A | Gdf | Pts | Form | ||||
| 1 | Ross County | 3 | 3 | 0 | 0 | 10 | 2 | +8 | 9 | WWW- | ||
| 2 | Forfar Athletic | 2 | 2 | 0 | 0 | 7 | 1 | +6 | 6 | WW-- | ||
| 3 | Montrose | 3 | 1 | 0 | 2 | 3 | 8 | -5 | 3 | LWL- | ||
| 4 | St.Johnstone | 2 | 0 | 0 | 2 | 1 | 3 | -2 | 0 | LL-- | ||
| 5 | Brechin City | 2 | 0 | 0 | 2 | 0 | 7 | -7 | 0 | LL-- | ||
| Saturday, 20 July 2019 | |||||
| 3 | Montrose | 1-4 | Forfar Athletic | ||
| 9(p) | Skelly | 25(p) | Hilson | ||
| 45(p) | Hilson | ||||
| 56 | Travis | ||||
| 71 | Travis | ||||
| Sunday, 21 July 2019 | |||||
| 3 | St.Johnstone | 1-2 | Ross County | ||
| 8(p) | Tanser | 30 | McKay | ||
| 45 | McKay | ||||
| Group C | Overall | |||||||||||
| P | W | D | L | F | A | Gdf | Pts | Form | ||||
| 1 | Arbroath | 2 | 2 | 0 | 0 | 8 | 2 | +6 | 6 | WW-- | ||
| 2 | 1 | Elgin City | 3 | 1 | 1 | 1 | 7 | 5 | +2 | 5 | WXL- | |
| 3 | 1 | Hibernian | 2 | 1 | 1 | 0 | 3 | 1 | +2 | 5 | WX-- | |
| 4 | Alloa Athletic | 2 | 0 | 1 | 1 | 3 | 5 | -2 | 1 | LX-- | ||
| 5 | Stirling Albion | 3 | 0 | 1 | 2 | 2 | 10 | -8 | 1 | LLX- | ||
| Saturday, 20 July 2019 | |||||
| 3 | Hibernian | 2-0 | Alloa Athletic | ||
| 68 | Doidge | ||||
| 84 | James | ||||
| 3 | Elgin City | 3-0 | Stirling Albion | ||
| 7 | Sutherland | ||||
| 13 | Hester | ||||
| 80 | Sutherland | ||||
| Group D | Overall | |||||||||||
| P | W | D | L | F | A | Gdf | Pts | Form | ||||
| 1 | Dundee | 3 | 1 | 2 | 0 | 3 | 0 | +3 | 7 | OOW- | ||
| 2 | Peterhead | 3 | 1 | 2 | 0 | 2 | 1 | +1 | 6 | OOW- | ||
| 3 | Inverness CT | 2 | 1 | 1 | 0 | 4 | 1 | +3 | 4 | WO-- | ||
| 4 | Cove Rangers | 2 | 0 | 1 | 1 | 1 | 2 | -1 | 1 | OL-- | ||
| 5 | Raith Rovers | 2 | 0 | 0 | 2 | 1 | 7 | -6 | 0 | LL-- | ||
| Saturday, 20 July 2019 | |||||
| 3 | Dundee | 0-0 | Peterhead | ||
| 3 | Inverness CT | 4-1 | Raith Rovers | ||
| 6 | White | 50 | Allan | ||
| 56 | Donaldson | ||||
| 58 | Doran | ||||
| 90 | Todorov | ||||
| Group E | Overall | |||||||||||
| P | W | D | L | F | A | Gdf | Pts | Form | ||||
| 1 | 1 | Motherwell | 2 | 2 | 0 | 0 | 7 | 0 | +7 | 6 | WW-- | |
| 2 | 2 | Queen of the South | 3 | 1 | 1 | 1 | 7 | 7 | +0 | 5 | WXL- | |
| 3 | 2 | Morton | 2 | 1 | 0 | 1 | 6 | 5 | +1 | 3 | LW-- | |
| 4 | 1 | Dumbarton | 3 | 1 | 0 | 2 | 3 | 10 | -7 | 3 | LLW- | |
| 5 | Annan Athletic | 2 | 0 | 1 | 1 | 3 | 4 | -1 | 1 | XL-- | ||
| Friday, 19 July 2019 | |||||
| 3 | Motherwell | 4-0 | Morton | ||
| 22 | Scott | ||||
| 66 | Scott | ||||
| 76 | Hylton | ||||
| 82 | Donnelly | ||||
| Saturday, 20 July 2019 | |||||
| 3 | Dumbarton | 1-4 | Queen of the South | ||
| 8 | Crossan | 10 | Paton | ||
| 13 | Oliver | ||||
| 17 | Dobbie | ||||
| 22 | Murray | ||||
| Group F | Overall | |||||||||||
| P | W | D | L | F | A | Gdf | Pts | Form | ||||
| 1 | Partick Thistle | 3 | 2 | 1 | 0 | 5 | 3 | +2 | 7 | XWW- | ||
| 2 | Hamilton | 3 | 1 | 2 | 0 | 5 | 3 | +2 | 6 | XWO- | ||
| 3 | 1 | Airdrieonians | 2 | 1 | 0 | 1 | 3 | 3 | +0 | 3 | WL-- | |
| 4 | 1 | Queen's Park | 2 | 0 | 1 | 1 | 1 | 2 | -1 | 2 | LO-- | |
| 5 | Clyde | 2 | 0 | 0 | 2 | 3 | 6 | -3 | 0 | LL-- | ||
| Saturday, 20 July 2019 | |||||
| 3 | Hamilton | 2-2 | Partick Thistle | ||
| 17 | Cunningham | 16 | Williamson | ||
| 54 | Cunningham | 73 | Gordon | ||
| Sunday, 21 July 2019 | |||||
| 3 | Clyde | 2-3 | Airdrieonians | ||
| 75(p) | Goodwillie | 34(p) | Roy | ||
| 85 | Goodwillie | 39 | Eckersley | ||
| 59 | Roy | ||||
| Group G | Overall | |||||||||||
| P | W | D | L | F | A | Gdf | Pts | Form | ||||
| 1 | 2 | Ayr United | 3 | 2 | 0 | 1 | 10 | 3 | +7 | 6 | WLW- | |
| 2 | 1 | Livingston | 2 | 1 | 1 | 0 | 3 | 2 | +1 | 5 | WX-- | |
| 3 | 1 | Falkirk | 3 | 1 | 1 | 1 | 3 | 3 | +0 | 4 | LWX- | |
| 4 | Stranraer | 2 | 1 | 0 | 1 | 6 | 1 | +5 | 3 | WL-- | ||
| 5 | Berwick Rangers | 2 | 0 | 0 | 2 | 0 | 13 | -13 | 0 | LL-- | ||
| Saturday, 20 July 2019 | |||||
| 3 | Ayr United | 2-1 | Falkirk | ||
| 26 | McCowan | 42 | McManus | ||
| 75 | Geggan | ||||
| 3 | Stranraer | 6-0 | Berwick Rangers | ||
| 19 | Elliott | ||||
| 38 | Allan | ||||
| 41 | McManus | ||||
| 45(p) | Stewart | ||||
| 63 | Hilton | ||||
| 75(p) | Stewart | ||||
| Group H | Overall | |||||||||||
| P | W | D | L | F | A | Gdf | Pts | Form | ||||
| 1 | Dunfermline | 3 | 2 | 0 | 1 | 9 | 3 | +6 | 6 | LWW- | ||
| 2 | St.Mirren | 3 | 1 | 1 | 1 | 3 | 3 | +0 | 4 | OWL- | ||
| 3 | 2 | FC Edinburgh | 2 | 1 | 0 | 1 | 1 | 1 | +0 | 3 | WL-- | |
| 4 | 1 | Albion Rovers | 2 | 1 | 0 | 1 | 1 | 6 | -5 | 3 | LW-- | |
| 5 | 1 | East Kilbride | 2 | 0 | 1 | 1 | 0 | 1 | -1 | 2 | OL-- | |
| Saturday, 20 July 2019 | |||||
| 3 | FC Edinburgh | 1-0 | Dunfermline | ||
| 87 | Handling | ||||
| 3 | East Kilbride | 0-0 | St.Mirren | ||
| 4 | Ross STEWART (Ross County) | |
| +2 | Shane SUTHERLAND (Elgin City) | |
| +2 | Billy McKAY (Ross County) | |
| 3 | +1 | Luke McCOWAN (Ayr United) |
| Kevin NISBET (Dunfermline) | ||
| +2 | Michael TRAVIS (Forfar Athletic) | |
| 2 | Kris DOOLAN (Ayr United) | |
| Kyle TURNER (Dunfermline) | ||
| +2 | David GOODWILLIE (Clyde, 1p) | |
| +1 | Connor MURRAY (Queen of the South) | |
| David GOLD (Arbroath) | ||
| +1 | Jermaine HYLTON (Motherwell) | |
| +2 | Ross CUNNINGHAM (Hamilton) | |
| Andrew NELSON (Dundee, 1p) | ||
| Greig SPENCE (Arbroath) | ||
| +1 | Declan McMANUS (Falkirk) | |
| +1 | Lawrence SHANKLAND (Dundee United) | |
| +2 | Mark STEWART (Stranraer, 2p) | |
| +1 | Stephen DOBBIE (Queen of the South) | |
| Michael MOFFAT (Ayr United) | ||
| +2 | Dale HILSON (Forfar Athletic, 2p) | |
| +2 | Alistair ROY (Airdrieonians, 1p) | |
| +1 | Liam DONNELLY (Motherwell, 1p) | |
| +2 | James SCOTT (Motherwell) | |
| +2 | Scott AGNEW (East Fife, 1p) |