The 2005–06 Scottish League Cup was the 60th staging of the Scotland's second most prestigious football knockout competition.
The competition was won by Celtic, who defeated Dunfermline Athletic 3–0 in the final.
First round Home teamScoreAway teamAlbion Rovers3–2GretnaStirling Albion2–1Queen of the SouthAlloa Athletic2–1ArbroathBerwick Rangers4–2Elgin CityBrechin City0–0Partick ThistleCowdenbeath2–3St JohnstoneEast Fife0–1StranraerEast Stirlingshire1–3Queen's ParkForfar Athletic1–4Ross CountyHamilton Academical2–1DumbartonMontrose0–1ClydeGreenock Morton1–2Ayr UnitedRaith Rovers2–0Airdrie UnitedStenhousemuir0–1Peterhead
Second round Home teamScoreAway teamInverness CT6–1Alloa AthleticAberdeen3–0Berwick RangersFalkirk2–1Partick ThistleAlbion Rovers1–3Dunfermline AthleticKilmarnock4–1Stirling AlbionMotherwell2–1Hamilton AcademicalPeterhead2–3ClydeQueen's Park0–2HeartsRaith Rovers1–2LivingstonRoss County1–2Ayr UnitedSt Johnstone0–1St MirrenStranraer3–1Dundee
Third round Home teamScoreAway teamAyr United1–2HibernianCeltic2–1FalkirkLivingston1–0HeartsInverness CT2–0Dundee UnitedKilmarnock3–4Dunfermline AthleticRangers5 – 2 ClydeSt Mirren0–2MotherwellStranraer0–2Aberdeen
Quarter-finals Home teamScoreAway teamCeltic2–0RangersDunfermline Athletic3–0HibernianLivingston2–1Inverness CTMotherwell1–0Aberdeen
Semi-finals
Final