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
1996–97 S.L. Benfica season week later; on the opening game of the Primeira Liga, Benfica drops two points against S.C. Braga in a home draw. Still, with two convincing wins in early September, Benfica reached top of the table, together with four other teams. With the second leg of the Supercup next, Benfica received Porto on 18 September. However, the contend quickly became an unbalanced one, with Porto scoring five goals to none, as Preud'Homme prevented an even darker outcome The team was not disturbed by this defeat, and continued racking up consecutive league wins, even achieving a two-point lead over the second place;