The 1999–2000 Taça de Portugal was the 60th edition of the Portuguese football knockout tournament, organized by the Portuguese Football Federation (FPF).
[1] The final was played on 21 May and replayed four days later as the inaugural match ended tied at the Estádio Nacional.
[3] The Auri-negros were eliminated in the fourth round by second division side Imortal.
[4] Porto defeated Sporting CP, 2–0 in the cup final replay to win their tenth Taça de Portugal.
[5][6] As a result of Porto winning the domestic cup competition, the Dragões faced 1999–2000 Primeira Liga winners Porto in the 2000 Supertaça Cândido de Oliveira.