1999–2000 Scottish League Cup

1999–00 Co-operative Insurance Cup
Tournament details
Country	Scotland
Final positions
Champions	Celtic
Runner-up	Aberdeen
	← 1998–99 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.

First round

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)

Second round

Home team	Score	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

Third round

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