Greek Cup 1998-99

The Greek Cup 1998–99 was the 57th edition of the Greek Football Cup, or Greek Cup for short. Olympiacos defeated Panathinaikos in the final on May 5, 1999.

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 (and only) team to lose the Cup final three times in a row.

The matches were held on November 8–12, 1998.

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