The 2008–09 FAW Welsh Cup was the 122nd season of the annual knockout tournament for competitive football teams in Wales, excluding those who play in the English League System. The 2008–09 tournament commenced on 16 August 2008, and was covered live and exclusive on S4C in the UK.
| Round | Date | Fixtures | width=100 | New entrants ! | Prize money |
|---|---|---|---|---|---|
| Preliminary Round | 16 August 2008 | 22 | 44 | ||
| First Round | 13 September 2008 | 46 | 70 | ||
| Second Round | 4 October 2008 | 32 | 18 | Losers: £500 | |
| Third Round | 1 November 2008 | 16 | Losers: £1,000 | ||
| Fourth Round | 31 January 2009 | 8 | Losers: £2,500 | ||
| Quarterfinals | 28 February 2009 | 4 | Losers: £5,000 | ||
| Semifinals | 11 April 2009 | 2 | Losers: £10,000 | ||
| Final | 4 May 2009 | 1 | Winner: £25,000; Loser: £15,000 |
The games were played on 16 August 2008.
|}1First match was postponed and the replay was held at Lock’s Lane, Porthcawl on 3 September 2008
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The matches were played on 13 September 2008.
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The matches were played between 3 and 10 October 2008.
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The matches were played on 31 October and 1 November 2008.
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The matches were played on 30 and 31 January 2009.
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