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
2006–07 S.L. Benfica season against Porto on 1 April. The visitors scored first through Pepe in the 41st minute, but Benfica equalized in the 83rd minute with an own-goal from Lucho González. Santos attributed the draw to Porto goalkeeper Helton's performance, saying, "Helton made three or four great saves. We were better in the second half and we deserved to win." On the following Thursday, Benfica visited the Olímpic de Montjuïc to face Espanyol. The Spaniards pushed hard from early on and scored first through Raúl Tamudo in the 15th minute; shortly after the half-hour mark, Albert Riera made it 2–0 and in the