| Macedonian Football Cup | |
| Year: | 2005–06 |
| Dates: | 31 July 2005 – 24 May 2006 |
| Num Teams: | 32 |
| Defending Champions: | Bashkimi |
| Champions: | Makedonija G.P. (1st title) |
| Runner-Up: | Shkëndija |
| Matches: | 45 |
| Goals: | 159 |
| Prevseason: | 2004–05 |
| Nextseason: | 2006–07 |
The 2005–06 Macedonian Football Cup was the 14th season of Macedonia's football knockout competition. Bashkimi were the defending champions, having won their first title. The 2005–06 champions were Makedonija G.P. who won their first title as well.
| Round | Date(s) | Fixtures | Clubs | New entries |
|---|---|---|---|---|
| First Round | 31 July 2005 | 16 | 32 → 16 | 32 |
| Second Round | 14 September & 19 October 2005 | 16 | 16 → 8 | none |
| Quarter-finals | 2 & 30 November 2005 | 8 | 8 → 4 | none |
| Semi-finals | 5 April & 10 May 2006 | 4 | 4 → 2 | none |
| Final | 24 May 2006 | 1 | 2 → 1 | none |
Matches were played on 31 July 2005.
|colspan="3" style="background-color:#97DEFF" align=center|31 July 2005|}
The first legs were played on 14 September and second were played on 19 October 2005.
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The first legs were played on 2 November and second were played on 30 November 2005.
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The first legs were played on 5 April and the second on 10 May 2006.
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Shkëndija 79 won 2–1 on aggregate.----
Makedonija G.P. won 3–2 on aggregate.