Celtic qualified for the knockout stage of the Champions League despite going down to a 1-0 defeat against AC Milan at the San Siro.
Benfica's 2-1 win over Shakhtar Donetsk in the Ukraine meant the Hoops could afford to lose and still go through - and Filippo Inzaghi's second-half strike ensured victory for Milan.
The home side started brightly with Massimo Ambrosini firing well wide from distance, while Kaka curled an effort past the post after Stephen McManus had carelessly given away possession 25 yards from his own goal.
After a stagnant period of play, Celtic mustered their first effort on goal in the 39th minute when Scott McDonald worked an opening for Jiri Jarosik - but the Hoops midfielder drilled his effort straight at Zeljko Kalac in the home goal.
Milan came out all guns blazing at the start of the second period, with Andrea Pirlo sending a swerving free-kick wide and Filippo Inzaghi missing the target from a tight angle.
But Gordon Strachan's men squandered a glorious chance to break the deadlock in the 56th minute when Scott Brown latched on to McManus' magnificent ball from the back but pulled his shot horribly wide from 14 yards with only the keeper to beat.
Milan should have taken the lead three minutes later when Inzaghi headed straight into the grateful arms of Artur Boruc from close range with the goal gapping.
However the Italian outfit finally took the lead with 20 minutes to go when Kaka played in Cafu down the right and the Brazilian veteran pulled his cross back for Inzaghi to sweep home from four yards.
Boruc made a superb double save to deny Cristian Brocchi and Inzaghi, while at the other end Brown worked an opening for himself and forced Kalac to make a smart stop at his near post as the Hoops pushed for an equaliser.
Substitute Jan Vennegor of Hesselink and Aiden McGeady both went close late on, but in the end defeat did not matter as Celtic booked their place in the last 16.
Oscar Cardozo scored twice for Benfica who claimed a place in the Uefa Cup after a 2-1 win over Shakhtar Donetsk.
Shakhtar had entertained hopes of still qualifying for the knockout stages of the Champions League for the first time but needed a victory, coupled with a Celtic defeat at already-qualified Milan to go through.