after an international break of nearly two weeks, benfica returned to competition on 10 september with a lisbon derby against sporting cp. koeman played the same 3–4–3 as before, selecting carlitos for the starting 11 in place of nuno gomes. sporting scored first through luís loureiro in the first half, but simão equalized with a free-kick on the second half. in the 75th minute, liédson made the score 2–1 against a ten-man benfica, ultimately winning the match for sporting. with two losses and a draw in three match-days, koeman broke a club record for the worst season start in history, already eight points from the top of the league. four days later, benfica made their seasonal european debut in the champions league against lille. the match was well fought between both teams, with fabrizio miccoli scoring a winning goal for benfica in the 92nd minute. koeman later said in the post-match interview, "we deserved this win because we search for it". on 18 september, benfica hosted união de leiria; koeman reverted to the 4–2–3–1 formation that giovanni trapattoni regularly used. benfica won 4–0 in the largest win all season, with nuno gomes netting a hat-trick. koeman classified the formation as "ideal," and sid he wanted to use it more often in the future. the following saturday, benfica played on the road against penafiel. a strong start put benfica in the lead by 2–0 in the first 15 minutes, and despite conceding a goal, they woth the match 3–1. koeman attributed the win to the good momentum that fabrizio miccoli–nuno gomes were passing. on 27 september, benfica travelled to old trafford to play manchester united on the second match-day of the champions league. united scored first through a ryan giggs free-kick that deflected off the wall; simão levelled the score in the second half—also on a free kick—but united responded with a winning goal in the 85th minute through ruud van nistelrooy.