1968–69 Scottish League Cup
The 1968–69 Scottish League Cup was the twenty-third season of Scotland's second football knockout competition. The competition was won for the fourth successive season by Celtic, who defeated Hibernian in the Final.
First round
Group 1
| Home Team | Score | Away Team | Date |
| Falkirk | 1–1 | Raith Rovers | 10 August 1968 |
| Hibernian | 0–1 | St Johnstone | 10 August 1968 |
| Raith Rovers | 0–1 | Hibernian | 14 August 1968 |
| St Johnstone | 2–3 | Falkirk | 14 August 1968 |
| Hibernian | 2–0 | Falkirk | 17 August 1968 |
| St Johnstone | 0–0 | Raith Rovers | 17 August 1968 |
| Raith Rovers | 4–2 | Falkirk | 24 August 1968 |
| St Johnstone | 2–2 | Hibernian | 24 August 1968 |
| Falkirk | 2–2 | St Johnstone | 28 August 1968 |
| Hibernian | 3–0 | Raith Rovers | 28 August 1968 |
| Falkirk | 0–2 | Hibernian | 31 August 1968 |
| Raith Rovers | 2–1 | St Johnstone | 31 August 1968 |
Group 2
| Home Team | Score | Away Team | Date |
| Airdrieonians | 2–3 | Heart of Midlothian | 10 August 1968 |
| Dundee | 4–0 | Kilmarnock | 10 August 1968 |
| Heart of Midlothian | 2–1 | Dundee | 14 August 1968 |
| Kilmarnock | 0–3 | Airdrieonians | 14 August 1968 |
| Dundee | 1–1 | Airdrieonians | 17 August 1968 |
| Kilmarnock | 3–3 | Heart of Midlothian | 17 August 1968 |
| Heart of Midlothian | 0–2 | Airdrieonians | 24 August 1968 |
| Kilmarnock | 2–2 | Dundee | 24 August 1968 |
| Airdrieonians | 2–0 | Kilmarnock | 28 August 1968 |
| Dundee | 4–0 | Heart of Midlothian | 28 August 1968 |
| Airdrieonians | 0–3 | Dundee | 31 August 1968 |
| Heart of Midlothian | 0–0 | Kilmarnock | 31 August 1968 |
Group 3
| Home Team | Score | Away Team | Date |
| Clyde | 4–1 | Aberdeen | 10 August 1968 |
| Dunfermline Athletic | 3–2 | Dundee United | 10 August 1968 |
| Aberdeen | 1–0 | Dunfermline Athletic | 14 August 1968 |
| Dundee United | 2–3 | Clyde | 14 August 1968 |
| Aberdeen | 4–1 | Dundee United | 17 August 1968 |
| Dunfermline Athletic | 2–1 | Clyde | 17 August 1968 |
| Aberdeen | 0–2 | Clyde | 24 August 1968 |
| Dundee United | 2–1 | Dunfermline Athletic | 24 August 1968 |
| Clyde | 0–4 | Dundee United | 28 August 1968 |
| Dunfermline Athletic | 1–2 | Aberdeen | 28 August 1968 |
| Clyde | 3–0 | Dunfermline Athletic | 31 August 1968 |
| Dundee United | 1–0 | Aberdeen | 31 August 1968 |
Group 4
| Home Team | Score | Away Team | Date |
| Morton | 1–3 | Partick Thistle | 10 August 1968 |
| Rangers | 0–2 | Celtic | 10 August 1968 |
| Celtic | 4–1 | Morton | 14 August 1968 |
| Partick Thistle | 1–5 | Rangers | 14 August 1968 |
| Celtic | 4–0 | Partick Thistle | 17 August 1968 |
| Rangers | 2–0 | Morton | 17 August 1968 |
| Celtic | 1–0 | Rangers | 24 August 1968 |
| Partick Thistle | 2–0 | Morton | 24 August 1968 |
| Morton | 0–3 | Celtic | 28 August 1968 |
| Rangers | 2–1 | Partick Thistle | 28 August 1968 |
| Morton | 0–5 | Rangers | 31 August 1968 |
| Partick Thistle | 1–6 | Celtic | 31 August 1968 |
Group 5
| Home Team | Score | Away Team | Date |
| Arbroath | 2–1 | Stirling Albion | 10 August 1968 |
| Ayr United | 3–1 | Cowdenbeath | 10 August 1968 |
| Cowdenbeath | 1–1 | Arbroath | 14 August 1968 |
| Stirling Albion | 2–4 | Ayr United | 14 August 1968 |
| Arbroath | 1–1 | Ayr United | 17 August 1968 |
| Stirling Albion | 2–1 | Cowdenbeath | 17 August 1968 |
| Cowdenbeath | 0–2 | Ayr United | 24 August 1968 |
| Stirling Albion | 1–0 | Arbroath | 24 August 1968 |
| Arbroath | 2–0 | Cowdenbeath | 28 August 1968 |
| Ayr United | 1–0 | Stirling Albion | 28 August 1968 |
| Ayr United | 3–1 | Arbroath | 31 August 1968 |
| Cowdenbeath | 3–6 | Stirling Albion | 31 August 1968 |
Group 6
| Home Team | Score | Away Team | Date |
| Berwick Rangers | 1–1 | Queen of the South | 10 August 1968 |
| East Fife | 2–0 | Clydebank | 10 August 1968 |
| Clydebank | 2–4 | Berwick Rangers | 14 August 1968 |
| Queen of the South | 1–1 | East Fife | 14 August 1968 |
| East Fife | 1–0 | Berwick Rangers | 17 August 1968 |
| Queen of the South | 1–2 | Clydebank | 17 August 1968 |
| Clydebank | 1–3 | East Fife | 24 August 1968 |
| Queen of the South | 2–0 | Berwick Rangers | 24 August 1968 |
| Berwick Rangers | 3–0 | Clydebank | 28 August 1968 |
| East Fife | 1–1 | Queen of the South | 28 August 1968 |
| Berwick Rangers | 1–4 | East Fife | 31 August 1968 |
| Clydebank | 1–1 | Queen of the South | 31 August 1968 |
Group 7
| Home Team | Score | Away Team | Date |
| Hamilton Academical | 2–1 | Motherwell | 10 August 1968 |
| Montrose | 1–2 | St Mirren | 10 August 1968 |
| Motherwell | 1–2 | Montrose | 14 August 1968 |
| St Mirren | 3–0 | Hamilton Academical | 14 August 1968 |
| Montrose | 0–2 | Hamilton Academical | 17 August 1968 |
| Motherwell | 6–0 | St Mirren | 17 August 1968 |
| Motherwell | 0–0 | Hamilton Academical | 24 August 1968 |
| St Mirren | 1–0 | Montrose | 24 August 1968 |
| Hamilton Academical | 2–1 | St Mirren | 28 August 1968 |
| Montrose | 2–1 | Motherwell | 28 August 1968 |
| Hamilton Academical | 2–0 | Montrose | 31 August 1968 |
| St Mirren | 2–0 | Motherwell | 31 August 1968 |
Group 8
| Home Team | Score | Away Team | Date |
| Dumbarton | 0–4 | Albion Rovers | 10 August 1968 |
| Queen's Park | 4–0 | Forfar Athletic | 10 August 1968 |
| Albion Rovers | 3–2 | Queen's Park | 14 August 1968 |
| Forfar Athletic | 1–0 | Dumbarton | 14 August 1968 |
| Albion Rovers | 2–4 | Forfar Athletic | 17 August 1968 |
| Dumbarton | 4–3 | Queen's Park | 17 August 1968 |
| Albion Rovers | 5–0 | Dumbarton | 24 August 1968 |
| Forfar Athletic | 0–2 | Queen's Park | 24 August 1968 |
| Dumbarton | 5–1 | Forfar Athletic | 28 August 1968 |
| Queen's Park | 2–3 | Albion Rovers | 28 August 1968 |
| Forfar Athletic | 2–2 | Albion Rovers | 31 August 1968 |
| Queen's Park | 1–0 | Dumbarton | 31 August 1968 |
Group 9
| Home Team | Score | Away Team | Date |
| Alloa Athletic | 0–1 | Stenhousemuir | 10 August 1968 |
| Stranraer | 2–1 | East Stirlingshire | 10 August 1968 |
| Brechin City | 2–3 | Alloa Athletic | 14 August 1968 |
| Stenhousemuir | 1–3 | Stranraer | 14 August 1968 |
| East Stirlingshire | 3–0 | Stenhousemuir | 17 August 1968 |
| Stranraer | 1–2 | Brechin City | 17 August 1968 |
| East Stirlingshire | 2–2 | Alloa Athletic | 24 August 1968 |
| Stenhousemuir | 1–0 | Brechin City | 24 August 1968 |
| Alloa Athletic | 0–1 | Stranraer | 31 August 1968 |
| Brechin City | 3–0 | East Stirlingshire | 31 August 1968 |