1998–99 Greek Football Cup
The 1998–99 Greek Football Cup was the 57th edition of the Greek Football Cup. Olympiacos defeated Panathinaikos in the final on May 5, 1999.Tournament details
In total, 60 teams participated: 18 from Alpha Ethniki, 18 from Beta, and 24 from Gamma. The competition was held over six rounds, included the final.
The first three rounds were single elimination matches. AEK Athens and PAOK, both of the Alpha Ethniki, were eliminated by lower division teams Poseidon Michaniona and Panserraikos respectively. As is typically seen in this tournament, half of the eight quarter-final teams came from Beta Ethniki. They were Kalamata, Panserraikos, Athinaikos and ILTEX Lykoi.
The final was contested in Athens at Olympic Stadium on May 5, 1999, by the eternal enemies, Olympiacos and Panathinaikos. They had last met in the Greek Cup Final in 1992-93. Panathinaikos had earlier eliminated Cup holders Panionios in the first round while Olympiacos had eliminated Ionikos by an impressive 4-7 score in the third round. Olympiacos won 2-0, their 20th Cup win. With the victory, Olympiacos achieved the Double for the first time in 18 years. With the Cup final loss, Panathinaikos became the first team to lose the Cup final three times in a row.First round
The matches were held on November 8-12, 1998.
| Home team | Score | Away team |
| Paniliakos | 6-1 | Agersani |
| Apollon Athens | 1-2 | Kozani |
| Marko | 6-2 | Apollon Kalamaria |
| Ethnikos Asteras | 1-2 | Aiolikos |
| EAR | 2-1 | Kilkisiakos |
| Aetos Skydra | 0-5 | PAOK |
| Anagennisi Karditsa | 4-2 | Apollon Krya Vrysi |
| Panachaiki | 2-0 | Veria |
| Karditsa A.C. | 4-0 | Levadiakos |
| ILTEX Lykoi | 2-0 | Achaiki |
| Xanthi | 2-0 | Kallithea |
| Athinaikos | 2-1 | Kastoria |
| Larissa | 3-0 | Proodeftiki |
| Ambelokipoi Thessaloniki | 3-1 | Doxa Drama |
| Iraklis | 4-1 | Nafpaktiakos Asteras |
| Naoussa | 0-2 | Aris |
| Panetolikos | 2-1 | Edessaikos |
| Panargiakos | 1-0 | Trikala |
| Atromitos | 0-1 | Kavala |
| Panelefsiniakos | 5-0 | Preveza |
| Ialysos | 1-0 | Keratsini |
| Olympiacos | 4-2 | Egaleo |
| Doxa Vyronas | 1-3 | OFI |
| Poseidon Michaniona | 1-0 | AEK Athens |
| Panserraikos | 2-1 | PAS Giannina |
| Pierikos | 0-1 | Kalamata |
| Panionios | 1-2 | Panathinaikos |
| Niki Volos | 1-2 | Ethnikos Piraeus |
| Agios Nikolaos | 0-0 | Panegialios |
| Olympiacos Volos | 1-1 | Ionikos |
Second round
The matches were held on December 16–17, 1998.
| Home team | Score | Away team |
| Panathinaikos | 2-1 | Panelefsiniakos |
| Kalamata | 2-0 | Marko |
| Kavala | 0-3 | Paniliakos |
| Karditsa A.C. | 2-1 | Panetolikos |
| ILTEX Lykoi | 2-1 | EAR |
| Panargiakos | 1-2 | Athinaikos |
| Aris | 1-3 | Olympiacos |
| Panegialios | 1-3 | PAOK |
| Larissa | 1-0 | Ambelokipoi Thessaloniki |
| Skoda Xanthi | 1-0 | Ethnikos Piraeus |
| OFI | 2-3 | Ionikos |
| Aiolikos | 0-0 | Anagennisi Karditsa |
| Poseidon Michaniona | 1-1 | Panachaiki |
| Ialysos | 2-2 | Iraklis |
| Panserraikos | bye | |
| Kozani | bye | |
Third round
The matches were held on January 12–13-14th 1999.
| Home team | Score | Away team |
| Ionikos | 4-7 | Olympiacos |
| Larissa | 0-2 | Athinaikos |
| PAOK | 0-1 | Panserraikos |
| ILTEX Lykoi | 5-1 | Kozani |
| Poseidon Michaniona | 1-2 | Iraklis |
| Skoda Xanthi | 2-0 | Karditsa A.C. |
| Aiolikos | 0-3 | Kalamata |
| Paniliakos | 0-2 | Panathinaikos |
Quarter-finals
First legs were held on January 27, February 10–11, 1999 and second legs on February 17–18.
| Team #1 | Agg. | Team #2 | 1st leg | 2nd leg |
| ILTEX Lykoi | 3–4 | Iraklis | 1–3 | 2–1 |
| Panserraikos | 0–5 | Panathinaikos | 0–3 | 0–2 |
| Olympiacos | 3–2 | Skoda Xanthi | 3–1 | 0–1 |
| Athinaikos | 1–1 | Kalamata | 0–0 | 1–1 |
Semi-finals
First legs were held on April 6–7, 1999, while second were held on 13th-14th.
| Team #1 | Agg. | Team #2 | 1st leg | 2nd leg |
| Panathinaikos | 8–3 | Athinaikos | 6–1 | 2–2 |
| Olympiacos | 5–1 | Iraklis | 4–0 | 1–1 |
Final
The 55th Greek Cup Final was played at the Athens Olympic Stadium "Spyridon Louis".
