| Greek Cup | |
| Year: | 2008–09 |
| Dates: | 30 August 2008 – 2 May 2009 |
| Num Teams: | 70 |
| Defending Champions: | Olympiacos |
| Champions: | Olympiacos (24th title) |
| Runner-Up: | AEK Athens |
| Matches: | 79 |
| Top Goal Scorer: | Ismael Blanco (5 goals) |
| Prevseason: | 2007–08 |
| Nextseason: | 2009–10 |
The 2008–09 Greek Football Cup was the 67th edition of the Greek Football Cup. The competition started on 30 August 2008 with the first round and concluded on 2 May 2009 with the final, held at Olympic Stadium.
Olympiacos claimed that season's Greek Cup, after a 4-4 draw and a 15–14 victory on penalties over AEK Athens, and was considered by fans as the most entertaining final in the tournament.[1] [2]
| Round | Date(s) | Fixtures | Clubs | New entries | Leagues entering |
|---|---|---|---|---|---|
| First Round | 30, 31 August & 7 September 2008 | 18 | 70 → 52 | 36 | Gamma Ethniki |
| Second Round | 16–18 September 2008 | 18 | 52 → 34 | 18 | Beta Ethniki |
| Additional Round | 24 September 2008 | 2 | 34 → 32 | none | none |
| Round of 32 | 28–30 October, 11–13 November 2008 | 16 | 32 → 16 | 16 | Super League |
| Round of 16 | 13–15, 20–22, 28 January 2009 | 12 | 16 → 8 | none | none |
| Quarter-finals | 4, 18, 25 February & 4 March 2009 | 8 | 8 → 4 | ||
| Semi-finals | 18 March & 8, 9 April 2009 | 4 | 4 → 2 | ||
| Final | 2 May 2009 | 1 | 2 → 1 |
Each tie in the knockout phase, apart from the quarter-finals and the semi-finals, was played by a single match. If the score was level at the end of normal time, extra time was played, followed by a penalty shoot-out if the score was still level. In the quarter-finals and the semi-finals were played over two legs, with each team playing one leg at home. The team that scored more goals on aggregate over the two legs advanced to the next round. If the aggregate score was level, the away goals rule was applied, i.e. the team that scored more goals away from home over the two legs advanced. If away goals were also equal, then extra time was played. The away goals rule was again applied after extra time, i.e. if there were goals scored during extra time and the aggregate score was still level, the visiting team advanced by virtue of more away goals scored. If no goals were scored during extra time, the winners were decided by a penalty shoot-out. In the round of 16, if the score was level at the end of normal time the two-legged rule was applied.
The mechanism of the draws for each round is as follows:
The draw took place on 18 August 2008.[3]
|-|colspan="3" style="background-color:#D0D0D0" align=center|30 August 2008|-|colspan="3" style="background-color:#D0D0D0" align=center|31 August 2008|}
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The draw took place on 18 August 2008, after the first-round draw.[3]
|-|colspan="3" style="background-color:#D0D0D0" align=center|16 September 2008|-|colspan="3" style="background-color:#D0D0D0" align=center|17 September 2008|-|colspan="3" style="background-color:#D0D0D0" align=center|18 September 2008|}
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The draw took place on 18 August 2008.[3]
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The draw took place on 19 November 2008.[4]
||colspan="2" ||colspan="2" rowspan="2" ||colspan="2" rowspan="3" |}
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The draw took place on 26 January 2009.[5]
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Olympiacos won 2–1 on aggregate.----AEK Athens won on away goals.----Asteras Tripolis won 2–0 on aggregate.----Panserraikos won 3–2 on aggregate.
The draw took place on 26 January 2009, after the quarter-final draw.[5]
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AEK Athens won 3–1 on aggregate.----Olympiacos won 4–3 on aggregate.
See main article: 2009 Greek Football Cup final.
| Rank | Player | Club | Goals |
|---|---|---|---|
| 1 |  Ismael Blanco | AEK Athens | 5 |
 Diogo | Olympiacos | ||
| 3 | Michalis Klokidis | Makedonikos | 4 |
| Lazaros Christodoulopoulos | Panathinaikos | ||
| 5 | Emanuel Perrone | Atromitos | 3 |
| Gilvan Carlos | Zakynthos | ||
| Matt Derbyshire | Olympiacos | ||
| Ante Rukavina | Panathinaikos | ||
| Ignacio Scocco | AEK Athens | ||
| 10 | Pavlos Leptokaridis | Anagennisi Giannitsa | 2 |
| Fabian Gerber | OFI | ||
 Marko Markovski | Kallithea | ||
 Nastja Čeh | Panserraikos | ||
| Anastasios Triantafyllou | Diagoras | ||
| Christos Kanellopoulos | Niki Volos | ||
| Ilias Siokos | Korinthos | ||
| Rogério Martins | Ergotelis | ||
| Facundo Parra | AEL | ||
| Vasilios Chatzivasiliadis | Kastoria | ||
| Danijel Cesarec | Asteras Tripolis | ||
| Stavros Tsoukalas | Doxa Drama | ||
 Victor Agali | Skoda Xanthi | ||
 Amr El Halwani | Veria | ||
| Petros Dimitriadis | Makedonikos | ||
| Ilias Manikas | Panetolikos | ||
 Ibrahima Bakayoko | PAOK | ||
| Israel Silva | Kerkyra | ||
 Bennard Yao Kumordzi | Panionios | ||
| Luciano Galletti | Olympiacos | ||
| Lucio Filomeno | Asteras Tripolis | ||
| Rafik Djebbour | AEK Athens | ||
| Vangelis Kaounos | Kalamata / Asteras Tripolis | ||
| Dudu Cearense | Olympiacos |