1999–2000 S.L. Benfica season "their worst performance of the season, and seeing Porto close in on the top of the table." On 4 November, Benfica hosted P.A.O.K. for the second leg of their European qualifier. They lost 2–1 in normal time, requiring extra time and a penalty shootout to decide the match. The Lisbon side converted all their shots, progressing into the next round. Four days later, the club defeated S.C. Braga by one goal in a league match to open a three-point lead. After a one-week break for the Taça de Portugal, Benfica visited Estádio das Antas for the Clássico against Porto. They
FC Porto in international football competitions decide the match 8–7 for Porto and give the club their second and last title in this competition. Despite the managerial instability – Fernández was replaced by José Couceiro soon after their Champions League elimination – and weak performances in league matches, Porto finished runners-up to Benfica and secured qualification for the 2005–06 UEFA Champions League group stage. Dutch coach Co Adriaanse was appointed as the new coach for the 2005–06 season, and although his team delivered domestically – reclaiming both Portuguese league and Cup titles – it disappointed in the Champions League, as Porto finished last of their group,