Celtic's dismal away record in the Champions League was extended as they lost to a late Oscar Cardozo goal against Benfica in Lisbon.
The Scottish champions matched the home side in the first half but after the break the Paraguayan international striker twice hit the woodwork and was denied by a world-class save from Artur Boruc.
But in the 86th minute Cardozo beat the offside trap to knock the ball past Boruc, leaving the Glasgow side 14 group games without a win away from Parkhead in the group stages.
The visitors can have little complaints after a second half which saw them enjoy some good fortune at the Estadio da Luz before they eventually succumbed late on. Qualification to the knockout stages now looks unlikely for the Glasgow side.
However Gordon Strachan felt his side had done enough to win the game. He said: "We had a couple of chances ourselves and on a lucky night I thought we might get the result. It's a very cruel game and you have to deal with it."
Midway through the first half, Aiden McGeady's short back-header to Gary Caldwell, intercepted in the penalty area by Leo, almost led to a Benfica opener. The Brazilian defender whipped the ball back but the onrushing Cardozo missed his kick.
Benfica started the second period brightly and in the 50th minute Boruc had to pull off a great save from a Cardozo header.
But Cardozo was not to be denied and in the 86th minute he knocked the ball past Boruc.
Benfica (4-4-2): Quim; Luisao, Leo, Pereira, Katsouranis; Costa, Assis (Di Maria, 61), Rodriguez (Luis Felipe, 84), Binya; Cardozo, Bergessio (Adu, 61). Substitutes not used: Ribieiro, Edcarlos, Zoro, Butt.
Celtic (4-4-2): Boruc; Caldwell,Kennedy, McManus, Naylor; Jarosik, Brown, Hartley, Donati (Sno, 63); McGeady, Killen (McDonald, 74). Substitutes not used: O'Brien, O'Dea, Nakamura, Balde, Brown.
Referee: M Busacca (Switzerland).
Results: Milan 2 Benfica 1; Shakhtar Donetsk 2 Celtic 0; Benfica 0 Shakhtar Donetsk 1; Celtic 2 Milan 1; Benfica 1 Celtic 0; Milan 4 Shakhtar Donetsk 1.
Remaining fixtures: 6 November: Celtic v Benfica; Shakhtar Donetsk v Milan. 28 November: Benfica v Milan; Celtic v Shakhtar Donetsk. 4 December: Milan v Celtic; Shakhtar Donetsk v Benfica.Reuse content