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
2004–05 S.L. Benfica season scored in the 13th minute. When asked why Anderlecht had more goal opportunities than Benfica, Trapattoni said, "Do you know international football? It is very balanced nowadays. I wish we had more chances but our opponent was stronger." Following the win, Benfica were due to meet Porto in the Supercup on 20 August. Ricardo Quaresma of Porto scored the only goal of the game in an individual effort. It was Benfica's tenth consecutive loss in the competition; the previous win occurred in 1989. Four days later, Benfica travelled to Belgium to play Anderlecht. The home team scored first by Aruna