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 days later, Benfica returned to the winning path in the Primeira Liga after beating Penafiel 4–0. Geovanni opened the scoring in the first half, after which Nuno Gomes, Simão and an own goal from Roberto set the final result. On 18 February, Benfica played on the road against Vitória de Guimarães. They did not play as expected and conceded two goals—one in each half—losing 2–0. The loss severely hampered their title defence after being overtaken by Sporting and Braga and allowing leaders Porto—their next league opponent—to gain an eight-point advantage. Three days after Guimarães, Benfica hosted Liverpool for the first