2005–06 Scottish League Cup#Semi-finals
{{Use British English|date=September 2014}}
{{Use dmy dates|date=September 2014}}
{{ infobox football tournament season
| title = 2005–06 Co-operative Insurance Cup
| image =
| imagesize =
| caption =
| country = Scotland
| num_teams =
| defending champions =
| champions = Celtic
| runner-up = Dunfermline Athletic
| matches =
| goals =
| top goal scorer =
| prevseason = 2004–05
| nextseason = 2006–07
}}
The 2005–06 Scottish League Cup was the 60th 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 Dunfermline Athletic 3–0 in the final.
First round
| class="wikitable" style="text-align: center" |
| width=140|Home team
!width=70|Score !width=140|Away team |
|---|
| Albion Rovers
|3–2 |
| Stirling Albion
|2–1 |
| Alloa Athletic
|2–1 |
| Berwick Rangers
|4–2 |
| Brechin City
|0–0 |
| Cowdenbeath
|2–3 |
| East Fife
|0–1 |
| East Stirlingshire
|1–3 |
| Forfar Athletic
|1–4 |
| Hamilton Academical
|2–1 |
| Montrose
|0–1 |
| Greenock Morton
|1–2 |
| Raith Rovers
|2–0 |
| Stenhousemuir
|0–1 |
Second round
| class="wikitable" style="text-align: center" |
| width=140|Home team
!width=70|Score !width=140|Away team |
|---|
| Inverness CT
|6–1 |
| Aberdeen
|3–0 |
| Falkirk
|2–1 |
| Albion Rovers
|1–3 |
| Kilmarnock
|4–1 |
| Motherwell
|2–1 |
| Peterhead
|2–3 |
| Queen's Park
|0–2 |
| Raith Rovers
|1–2 |
| Ross County
|1–2 |
| St Johnstone
|0–1 |
| Stranraer
|3–1 |
Third round
| class="wikitable" style="text-align: center" |
| width=140|Home team
!width=70|Score !width=140|Away team |
|---|
| Ayr United
|1–2 |
| Celtic
|2–1 |
| Livingston
|1–0 |
| Inverness CT
|2–0 |
| Kilmarnock
|3–4 |
| Rangers
|5 – 2 |
| St Mirren
|0–2 |
| Stranraer
|0–2 |
Quarter-finals
| class="wikitable" style="text-align: center" |
| width=140|Home team
!width=70|Score !width=140|Away team |
|---|
| Celtic
|2–0 |
| Dunfermline Athletic
|3–0 |
| Livingston
|2–1 |
| Motherwell
|1–0 |
Semi-finals
{{football box |
|date = 25 January 2006
|team1 = Dunfermline Athletic
|score = 1–0
|report = [http://news.bbc.co.uk/sport1/hi/football/scot_cups/4642756.stm Report]
|team2 = Livingston
|goals1 = Harris {{goal|37|pen.}}
|goals2 =
|stadium = Easter Road, Edinburgh
|referee = Dougie McDonald
|attendance = 14,630 }}
----
{{football box |
|date = 1 February 2006
|team1 = Motherwell
|score = 1–2
|report = [http://news.bbc.co.uk/sport1/hi/football/scot_cups/4666800.stm Report]
|team2 = Celtic
|goals1 = Foran {{goal|11}}
|goals2 = Żurawski {{goal|29}}
Maloney {{goal|88}}
|stadium = Hampden Park, Glasgow
|referee = Craig Thomson
|attendance = 42,595 }}
Final
{{main|2006 Scottish League Cup Final}}
{{football box |
|date = 19 March 2006
|team1 = Dunfermline Athletic
|score = 0–3
|report = [http://news.bbc.co.uk/sport1/hi/football/scot_cups/4807338.stm Report]
|team2 = Celtic
|goals1 =
|goals2 = Żurawski {{goal|43}}
Maloney {{goal|76}}
Dublin {{goal|90}}
|stadium = Hampden Park, Glasgow
|referee = Stuart Dougal
|attendance = 52,103 }}
{{Scottish League Cup seasons}}
{{2005-06 in Scottish football}}
{{2005–06 in European football (UEFA)}}
{{DEFAULTSORT:2005-06 Scottish League Cup}}