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2006 League of Ireland Cup
| runner-up = | semi-finalist1 = | semi-finalist2 =
The League of Ireland Cup 2006 was the 33rd staging of the League of Ireland Cup.
The 2006 League Cup kicked off in April. Sixteen league clubs and the Kerry League entered the competition. There were two clubs drawn to face each other in the first round, with the rest given byes to the second round.
First round
Match played on 3 April 2006.
| Tie no | Home team | Score | Away team | Finn Harps won 2–1 on penalties |
|---|---|---|---|---|
| 1 | Finn Harps | 1–1 | Galway United |
Second round
Matches played between 2 May and 10 May 2006.
| Tie no | Home team | Score | Away team | Finn Harps won 5–4 on penalties |
|---|---|---|---|---|
| 1 | St Patrick's Athletic | 0–2 | Shamrock Rovers | |
| 2 | Dublin City | 0–1 | Shelbourne | |
| 3 | Dundalk | 0–1 | Drogheda United | |
| 4 | Derry City | 1–0 | Longford Town | |
| 5 | Monaghan United | 0–2 | Bohemians | |
| 6 | Sligo Rovers | 1–1 | Finn Harps | |
| 7 | Cork City | 0–1 | Cobh Ramblers | |
| 8 | Limerick | 1–0 | Kerry League |
Quarter-finals
Matches played on 4 July and 5 July 2006.
| Tie no | Home team | Score | Away team |
|---|---|---|---|
| 1 | Bohemians | 1–0 | Cobh Ramblers |
| 2 | Derry City | 4–0 | Drogheda United |
| 3 | Limerick | 1–0 | Shamrock Rovers |
| 4 | Shelbourne | 4–1 | Finn Harps |
Semi-finals
O'Flynn |
Final
(a.e.t) Derry City won 3–0 on penalties
| League of Ireland Cup Winner 2006 |
|---|
| Derry City |
| 7th Title |
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