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 losing the game. Benfica ended the season in third place, missing out on the title and an automatic place in the 2006–07 UEFA Champions League. Despite winning both games against Porto, the closest Benfica had come from them was on the 18 and 19 match-days, with only three points. Benfica closed the season 12 points behind the leader and five from Sporting. Of the Big Three, Benfica conceded the most goals (29) and scored the second-highest number of goals (51), with the worst goal-average (+22). Koeman wanted to fulfil his contract with Benfica, but after negotiations with the management and