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 teamScoreAway teamAlbion Rovers (4)0–3Clyde (3)Brechin City (4)0–2Dumbarton (4)Clydebank (2)1–2East Stirlingshire (4)Cowdenbeath (4)0–2Livingston (2)East Fife (4)2–2Stirling Albion (3)Montrose (4)1–2Hamilton Academical (3)Partick Thistle (3)0–2Alloa Athletic (3)Queen of the South (3)1–0Arbroath (3)Queen's Park (4)2–1Berwick Rangers (4)Ross County (3)2–1Forfar Athletic (3)Stenhousemuir (3)1–3Inverness Caledonian Thistle (2)Stranraer (3)0–1Raith Rovers (2)
Second round Home teamScoreAway teamGreenock Morton1–3Alloa AthleticInverness Caledonian Thistle2–0St MirrenEast Fife(p)2–2AirdrieoniansDundee4–0DumbartonClyde2–2(p)HibernianAyr United2–1HamiltonAberdeen1–0LivingstonRaith Rovers2–2MotherwellQueen of the South1–3HeartsEast Stirlingshire0–2FalkirkDunfermline Athletic4–0Queen's ParkDundee United3–1Ross County
Third round Home teamScoreAway teamAyr United0–4CelticAberdeen(p)1–1FalkirkAlloa Athletic1–3DundeeEast Fife0–2HeartsInverness Caledonian Thistle0–1MotherwellKilmarnock3–2HibernianRangers1–0Dunfermline AthleticSt Johnstone1–2Dundee United
Quarter-finals Home teamScoreAway teamKilmarnock1–0HeartsAberdeen1–0RangersCeltic1–0DundeeDundee United3–2Motherwell
Semi-finals
Final
External links Scottish League Cup 1999/2000