SL Benfica thought they had done enough to live another day in the UEFA Champions League after coming from behind to draw 1-1 with AC Milan, only for a late goal in Glasgow to send the holders through and the Portuguese club out.
The Eagles were still in contention for the knockout rounds when the final whistle blew at the Estádio do Sport Lisboa e Benfica, Andrea Pirlo and Maxi Pereira having traded superb first-half goals, but the celebrations were curtailed when news filtered through that Celtic FC had scored an added-time winner against FC Shakhtar Donetsk. Benfica must now prevail in Ukraine on Matchday 6 to reach the UEFA Cup, while Milan entertain the Scottish team requiring a point to win Group D.
If the Benfica players had shown their determation to get their campaign back on track by huddling together before kick-off, their unity was undermined by a nervous start. Alberto Gilardino spurned an excellent chance in the second minute having been picked out by Cristian Brocchi's right-wing cross. Two minutes later and Quim was forced into action by Clarence Seedorf, turning the Dutchman's shot around the post after his one-two with Gilardino.
It was little surprise, then, when the European champions took the lead on the quarter-hour. Milan built patiently down the left, although the dynamic of the attack changed once Kaká played the ball to Pirlo and the Italy midfielder ran unchallenged before swerving a magnificent low strike into the corner of the net from distance. Pirlo almost conjured a second goal for the visitors three minutes later, Quim having to intervene as Petit nearly turned a free-kick from the Milan man into his own goal.
Home hopes still alive, Benfica hit back in the 20th minute. Rui Costa and Konstantinos Katsouranis played the ball from left to right to Pereira, who showed a lovely touch to cut inside Gennaro Gattuso before arrowing a rising shot from outside the box beyond Dida and in off the post. It was real end-to-end stuff now, David Luiz denying Kaká in one area with a sliding challenge after a swift counterattack; Cristián Rodríguez twice going close in the other.
Kakha Kaladze then cleared a 38th-minute Pereira shot behind with Dida grounded as Benfica upped the tempo, prompting Milan coach Carlo Ancelotti to introduce Paolo Maldini for Serginho at half-time. Another change quickly followed, Yoann Gourcuff replacing the injured Brocchi, and the newcomers were able to settle as the frenetic pace of the first period dropped.
Rui Costa, facing his former club, was the most influential player of the second half, showing a full array of tricks and flicks, yet it was only in the closing few minutes that the game truly reignited. Dida made a couple of nervy stops before Kaká scuffed a shot wide when unmarked after charging into the box in the last minute. The Brazilian had an equally presentable opening in added time but headed wide – Benfica's fate, though, would soon be settled by events elsewhere.