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
2001–02 S.L. Benfica season hosted Braga with Jankauskas, Simão and Sokota all sidelined by injuries. Without any firepower, the team took a 1–1 draw, allowing Porto to catch up in the league race. Benfica opened April in Azores against Santa Clara on the 6th. Lacking attacking options, the team was unable to score and ended with a goalless draw; they remained ahead of Porto only with the goal difference. On 14 April, Benfica received Paços de Ferreira at home. With two goals in the first half and another two in the second, the team won 4–0 and remained in third. A week later, Benfica