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
2005–06 S.L. Benfica season for Benfica in the 20th minute, but Tiago Targino equalized a few minutes later. Simão put Benfica back in front with a deflected shot that beat Márcio Paiva, ensuring a third consecutive win that reduced the distance to the league leader to four points. After another interruption for international football, Benfica returned to competition with a Clássico against Porto. Despite Porto being the favourite to win, Benfica won 2–0 with two goals from Nuno Gomes. It was Benfica's first away win at Porto since 1990–91, when César Brito also scored a double. On the following Thursday, Benfica visited El Madrigal