FC Porto in the 2008–09 season, Porto was on course to emulate the "Penta" of the late 1990s, but the series was broken by Benfica in the following season. Although Ferreira won his first Supertaça and defended the Taça de Portugal title, the team's failure to claim a fifth consecutive league – finishing third, outside the Champions League-qualifying places – and a 3–0 defeat against Benfica in the final of the Taça da Liga contributed to his resignation at the end of the season. A home win against Benfica prevented the rivals from celebrating the league title at the Estádio do Dragão.
2005–06 S.L. Benfica season days later, Benfica returned to the winning path in the Primeira Liga after beating Penafiel 4–0. Geovanni opened the scoring in the first half, after which Nuno Gomes, Simão and an own goal from Roberto set the final result. On 18 February, Benfica played on the road against Vitória de Guimarães. They did not play as expected and conceded two goals—one in each half—losing 2–0. The loss severely hampered their title defence after being overtaken by Sporting and Braga and allowing leaders Porto—their next league opponent—to gain an eight-point advantage. Three days after Guimarães, Benfica hosted Liverpool for the first