| 2005–06 Co-operative Insurance Cup | |
| Country: | Scotland |
| Champions: | Celtic |
| Runner-Up: | Dunfermline Athletic |
| Prevseason: | 2004–05 |
| Nextseason: | 2006–07 |
The 2005–06 Scottish League Cup was the 60th staging of the Scotland's second most prestigious football knockout competition, also known for sponsorship reasons as the CIS Insurance Cup.
The competition was won by Celtic, who defeated Dunfermline Athletic 3–0 in the final.
| width=140 | Home team | width=70 | Score | width=140 | Away team |
|---|---|---|---|---|---|
| Albion Rovers | 3–2 | Gretna | |||
| Stirling Albion | 2–1 | Queen of the South | |||
| Alloa Athletic | 2–1 | Arbroath | |||
| Berwick Rangers | 4–2 | Elgin City | |||
| Brechin City | 0–0 | Partick Thistle | |||
| Cowdenbeath | 2–3 | St Johnstone | |||
| East Fife | 0–1 | Stranraer | |||
| East Stirlingshire | 1–3 | Queen's Park | |||
| Forfar Athletic | 1–4 | Ross County | |||
| Hamilton Academical | 2–1 | Dumbarton | |||
| Montrose | 0–1 | Clyde | |||
| Greenock Morton | 1–2 | Ayr United | |||
| Raith Rovers | 2–0 | Airdrie United | |||
| Stenhousemuir | 0–1 | Peterhead |
| width=140 | Home team | width=70 | Score | width=140 | Away team |
|---|---|---|---|---|---|
| Inverness CT | 6–1 | Alloa Athletic | |||
| Aberdeen | 3–0 | Berwick Rangers | |||
| Falkirk | 2–1 | Partick Thistle | |||
| Albion Rovers | 1–3 | Dunfermline Athletic | |||
| Kilmarnock | 4–1 | Stirling Albion | |||
| Motherwell | 2–1 | Hamilton Academical | |||
| Peterhead | 2–3 | Clyde | |||
| Queen's Park | 0–2 | Hearts | |||
| Raith Rovers | 1–2 | Livingston | |||
| Ross County | 1–2 | Ayr United | |||
| St Johnstone | 0–1 | St Mirren | |||
| Stranraer | 3–1 | Dundee |
| width=140 | Home team | width=70 | Score | width=140 | Away team |
|---|---|---|---|---|---|
| Ayr United | 1–2 | Hibernian | |||
| Celtic | 2–1 | Falkirk | |||
| Livingston | 1–0 | Hearts | |||
| Inverness CT | 2–0 | Dundee United | |||
| Kilmarnock | 3–4 | Dunfermline Athletic | |||
| Rangers | 5 – 2 | Clyde | |||
| St Mirren | 0–2 | Motherwell | |||
| Stranraer | 0–2 | Aberdeen |
| width=140 | Home team | width=70 | Score | width=140 | Away team |
|---|---|---|---|---|---|
| Celtic | 2–0 | Rangers | |||
| Dunfermline Athletic | 3–0 | Hibernian | |||
| Livingston | 2–1 | Inverness CT | |||
| Motherwell | 1–0 | Aberdeen |
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See main article: 2006 Scottish League Cup Final.