The Cypriot Cup 2008–09 started on September 23, 2008. The format of the competition has been changed for this season. There was not a group stage and only teams from the first and second division participated (28 teams total). Teams from the lower divisions (third and fourth) competed in a separate cup competition. The Cypriot cup was completed in 5 rounds. All rounds were two-legged except the final.

Bracket

First round

The draw for the First Round took place on September 10, 2008 in the Hilton Park hotel in Nicosia

Nicosia

Nicosia from , known locally as Lefkosia , is the capital and largest city in Cyprus, as well as its main business center. Nicosia is the only divided capital in the world, with the southern and the northern portions divided by a Green Line...

. The first legs were played on September 23, 24 and October 1, 2008. The second legs were played on October 4 and 5, 2008.
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Second round

Teams that qualified for last year

Cypriot Cup 2007-08

The Cypriot Cup 2007–08 was the 66th edition of The Cypriot Football Cup, or Cypriot Cup for short. 16 clubs' entries were accepted for the competition.The competition culminated with the Cup Final, held at GSP Stadium, Nicosia on 17 May 2008...

's semifinals entered in this round, along with the 12 winners of the previous round. The draw for the second round took place on December 29, 2008. The first legs were played on January 14 and 21, 2009. The second legs were played on January 28 and February 4, 2009.
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Quarterfinals

The draw for the quarterfinals took place on February 5, 2009 at the Hilton Park hotel in Nicosia. The first legs were played on February 25 and March 4, 2009. The second legs were played on March 11 and 18, 2009.
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Semifinals

The draw for the semifinals took place at the Hilton Park hotel in Nicosia on March 20, 2009. The first legs were played on April 15, 2009. The second legs were played on May 6, 2009.

First legs

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Second legs

AEL won 3–2 on aggregate
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APOP Kinyras Peyias won 2–1 on aggregate

Final

See also

• Cypriot First Division 2008–09
• Cypriot Second Division 2008–09