1999–00 Co-operative Insurance Cup
Tournament details
CountryScotland
Final positions
ChampionsCeltic
Runner-upAberdeen

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

Quarter-finals

Home team Score Away team
Kilmarnock 1–0 Hearts
Aberdeen 1–0 Rangers
Celtic 1–0 Dundee
Dundee United 3–2 Motherwell

Semi-finals

Aberdeen1–0Dundee United
Stavrum 78' Report
Dens Park, Dundee
Attendance: 9,500
Referee: John Rowbotham

Celtic1–0Kilmarnock
Moravcik 66' Report
Hampden Park, Glasgow
Attendance: 22,926
Referee: Jim McCluskey

Final

Aberdeen0–2Celtic
Riseth 15'
Johnson 58'
Hampden Park, Glasgow
Attendance: 50,073
Referee: Kenny Clark
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