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
1999–2000 S.L. Benfica season benefited from the points-share and Benfica fell to six points behind Porto. On 12 January the club hosted Amora for the Portuguese Cup, scoring seven goals against the third-tier team. Three days later, Benfica visited Funchal and nearly lost; "Record" labelled Enke's performance as crucial for Benfica, illustrating, "In the key moment of the game, when Enke defended a penalty in the 10th minute, he saved Benfica from leaving Funchal with a defeat. In a sluggish performance, only new signings Uribe and Machairidis showed good form." On Matchday 18, Benfica hosted Rio Ave, winning their first league game in a