2005–06 Scottish Cup
The 2005–06 Scottish Cup was the 121st season of Scotland's most prestigious football knockout competition, also known for sponsorship reasons as the Tennent's Scottish Cup. The Cup was won by SPL club Heart of Midlothian who defeated Second Division side Gretna on penalties after a 1–1 draw in the final. Gretna earned a place in the UEFA Cup with Hearts having already qualified for the Champions League via the SPL.
A major shock occurred in the third round when First Division side Clyde defeated Cup holders Celtic 2–1. Rangers were knocked out of at the fourth round stage, losing 3–0 at home to Hibernian. Spartans reached the fourth round before eventually losing to St Mirren after a replay.
Fourth round
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Replays
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Quarter-finals
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Semi-finals
----Largest Wins
A list of the largest wins from the competition.| Score | Home Team | Away Team | Stage |
| 9-0 | Alloa Athletic | Selkirk | First Round |
| 6-0 | Hibernian | Arbroath | Third Round |
| 6-1 | Gretna | Cove Rangers | Second Round |
| 5-0 | Rangers | Peterhead | Third Round |
| 5-0 | Ross County | Forfar Athletic | Third Round |
| 0-5 | Lossiemouth | Spartans | Second Round |