| Tournament details | |
|---|---|
| Country | Scotland |
| Final positions | |
| Champions | Celtic |
| Runners-up | Aberdeen |
The1999–2000Scottish League Cup was the 54th staging of the Scotland's second most prestigiousfootball knockout competition, also known for sponsorship reasons as theCIS Insurance Cup.
The competition was won byCeltic, who defeatedAberdeen 2–0 inthe Final.
| Home team | Score | 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) |
| Home team | Score | 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 |
| Home team | Score | Away team |
|---|---|---|
| Kilmarnock | 1–0 | Hearts |
| Aberdeen | 1–0 | Rangers |
| Celtic | 1–0 | Dundee |
| Dundee United | 3–2 | Motherwell |
