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
2003–04 S.L. Benfica season his presentation, he confessed that the club's limited finances would make it harder to sign players; he also said that Benfica would give their best but did not expect to dethrone Porto. Benfica inquired after Helton, and Ricardo to compete with José Moreira for the goalkeeper position. Over the course of two weeks, the club negotiated unsuccessfully with the latter and ultimately chose to stay with Moreira. The club also looked into strengthen their options at centre and at left-back, negotiating unsuccessfully with Ânderson Polga, Atouba and Júnior. Despite these failed negotiations, Benfica added Luisão, and re-signed Geovanni; both would