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
2002–03 S.L. Benfica season Setúbal on 5 October, dropping two points in a 1–1 draw, due to a "childish error, or better yet, a lack of sharpness of the back-four", in the words of Ricardo Tavares from "Record". On 20 October, Benfica met Porto in Estádio das Antas for the "Clássico". It was an intense match, with 3 ejections and 73 fouls. Porto won 2–1 because to António Tadeira, they "reacted better to playing outnumbered, while Benfica lost their focus when Paulo Costa sent off Éder and then Miguel". Six days later, for the final game of the month, Benfica played Académica at home.