| 1999–00 Co-operative Insurance Cup | |
| Country: | Scotland |
| Champions: | Celtic |
| Runner-Up: | Aberdeen |
| Prevseason: | 1998–99 |
| Nextseason: | 2000–01 |
The 1999–2000 Scottish League Cup was the 54th 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 Aberdeen 2–0 in the Final.
| width=170 | Home team | width=70 | Score | width=170 | Away team |
|---|---|---|---|---|---|
| Albion Rovers (4) | 0–3 | Clyde (3) | |||
| Brechin City (4) | 0–2 | Dumbarton (4) | |||
| Clydebank (2) | 1–2 | East Stirlingshire (4) | |||
| Cowdenbeath (4) | 0–2 | Livingston (2) | |||
| East Fife (4) | 2–2 | Stirling Albion (3) | |||
| Montrose (4) | 1–2 | Hamilton Academical (3) | |||
| Partick Thistle (3) | 0–2 | Alloa Athletic (3) | |||
| Queen of the South (3) | 1–0 | Arbroath (3) | |||
| Queen's Park (4) | 2–1 | Berwick Rangers (4) | |||
| Ross County (3) | 2–1 | Forfar Athletic (3) | |||
| Stenhousemuir (3) | 1–3 | Inverness Caledonian Thistle (2) | |||
| Stranraer (3) | 0–1 | Raith Rovers (2) |
| width=170 | Home team | width=70 | Score | width=170 | Away team |
|---|---|---|---|---|---|
| Greenock Morton | 1–3 | Alloa Athletic | |||
| Inverness Caledonian Thistle | 2–0 | St Mirren | |||
| East Fife | (p)2–2 | Airdrieonians | |||
| Dundee | 4–0 | Dumbarton | |||
| Clyde | 2–2(p) | Hibernian | |||
| Ayr United | 2–1 | Hamilton | |||
| Aberdeen | 1–0 | Livingston | |||
| Raith Rovers | 2–2 | Motherwell | |||
| Queen of the South | 1–3 | Hearts | |||
| East Stirlingshire | 0–2 | Falkirk | |||
| Dunfermline Athletic | 4–0 | Queen's Park | |||
| Dundee United | 3–1 | Ross County |
| width=170 | Home team | width=70 | Score | width=170 | Away team |
|---|---|---|---|---|---|
| Ayr United | 0–4 | Celtic | |||
| Aberdeen | (p)1–1 | Falkirk | |||
| Alloa Athletic | 1–3 | Dundee | |||
| East Fife | 0–2 | Hearts | |||
| Inverness Caledonian Thistle | 0–1 | Motherwell | |||
| Kilmarnock | 3–2 | Hibernian | |||
| Rangers | 1–0 | Dunfermline Athletic | |||
| St Johnstone | 1–2 | Dundee United |
| width=140 | Home team | width=70 | Score | width=140 | Away team |
|---|---|---|---|---|---|
| Kilmarnock | 1–0 | Hearts | |||
| Aberdeen | 1–0 | Rangers | |||
| Celtic | 1–0 | Dundee | |||
| Dundee United | 3–2 | Motherwell |
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See main article: 2000 Scottish League Cup Final.