Challenge Cup| ROUND | R1 | R2 | R3 | QF | SF | F | |
| N | S | ||||||
| Season archive |
| Northern Section | ||||||
| Tuesday, 14 August 2018 | ||||||
| r1 | Raith Rovers | 3-1 | Aberdeen U20 | |||
| r1 | Cowdenbeath | 1-3 | East Fife | |||
| r1 | Inverness CT | 1-2 | Dunfermline | |||
| r1 | Alloa Athletic | 3-1 | Stirling Albion | |||
| r1 | Peterhead | 2-1 | Brechin City | |||
| r1 | Inverurie Locos | 0-1 | Formartine United | |||
| r1 | Hearts B | 1-2 | Ross County | |||
| r1 | Dundee U20 | 2-2 | Hibernian U20 | p4-3 | ||
| Wednesday, 15 August 2018 | ||||||
| r1 | Dundee United | 3-2 | St.Johnstone U20 | |||
| r1 | Elgin City | 1-1 | Arbroath | p6-7 | ||
| r1 | Cove Rangers | 2-2 | Montrose | p3-4 | ||
| Tuesday, 21 August 2018 | ||||||
| r1 | Livingston U20 | 0-0 | Forfar Athletic | p5-4 | ||
| Southern Section | ||||||
| Tuesday, 14 August 2018 | ||||||
| r1 | Stranraer | 0-5 | Partick Thistle | |||
| r1 | Berwick Rangers | 0-3 | Airdrieonians | |||
| r1 | Queen's Park | 0-0 | Ayr United | p4-2 | ||
| r1 | East Stirlingshire | 0-3 | Motherwell U20 | |||
| r1 | Stenhousemuir | 0-3 | Queen of the South | |||
| r1 | Dumbarton | 2-1 | Morton | |||
| r1 | Edinburgh City | 3-1 | Albion Rovers | |||
| r1 | Annan Athletic | 4-0 | Celtic B | |||
| r1 | Hamilton U20 | 4-1 | Clyde | |||
| r1 | Kilmarnock U20 | 1-2 | St.Mirren U20 | |||
| r1 | Rangers B | 1-2 | Falkirk | |||
| Wednesday, 15 August 2018 | ||||||
| r1 | East Kilbride | 1-1 | Spartans | p5-4 | ||
| 2 | +2 | Mason BLOOMFIELD (Hamilton U20) |
| +2 | Callum HENDRY (St.Johnstone U20) | |
| +2 | Stephen DOBBIE (Queen of the South) | |
| +2 | Billy McKAY (Ross County) | |
| +2 | Ross FERGUSSON (Annan Athletic) | |
| +2 | Blair HENDERSON (Edinburgh City, 1p) | |
| +2 | Kevin CAWLEY (Alloa Athletic) | |
| +2 | Aidan FITZPATRICK (Partick Thistle) | |
| +2 | Paul McMULLAN (Dundee United) | |
| +2 | Tony WALLACE (Annan Athletic) | |
| +2 | Paul McMANUS (Cove Rangers) |
