Milan failed to convert any of their penalties in the shoot-out after a 2-2 draw with Internacional in the Audi Cup.
Having lost to Bayern Munich on penalties last night, drawing 1-1 after 90 minutes, Massimiliano Allegri's men faced Brazil's Internacional for third place in the German tournament.
The Rossoneri took a very early lead against Bayern Munich with Ibrahimovic and repeated the trick in this game.
Within the opening three minutes, a corner had been well played down the right with Robinho pulling back for a cheeky Ibrahimovic backheel flick.
Internacional are already 12 games into the Brazilian season and found an equaliser on the counter-attack with Leandro Damião, who finished off from five yards after Gilberto sprinted past Mario Yepes down the right.
Robinho, João Paulo and Alexandre Pato threatened. Pato should've scored against his former club straight after the break, as Ibra dispossessed a defender at the by-line and Robinho rolled across, but The Duck smacked his angled drive against the post.
Pato made up for it on the hour mark, as a Robinho-Ibrahimovic give-and-go sent the Brazilian clear to stroke home.
It should've been 3-1 moments later with another well-worked move, but Renan did well to deny Pato from point-blank range.
However, Internacional equalised 10 minutes from time with substitute Andres D'Alessandro. João Paulo's shot took a ricochet off Thiago Silva to accidentally set up D'Alessandro with only Flavio Roma to beat.
Youth team player Valoti could've won it at the death from an Antonio Cassano nutmeg assist, but fired right at the goalkeeper at the near post.
Once again, it went to penalties. Against Bayern it was Milan who converted four before Alberto Paloschi missed the decider. This time, all four of the Rossoneri players failed to convert with Valoti, Cassano and Pato's efforts saved, while Massimo Oddo hit the post.
Internacional 2-2 Milan
Scorers: Ibrahimovic 3 (M), Leandro Damião 23 (I), Pato 60 (M), D'Alessandro 80 (I)
Internacional: Renan; Glaydson, Bolívar, Dalton, Fabrício (Kleber 86); Wilson Matias, Élton (Nei 67), Zé Mário, João Paulo; Gilberto (Roggia 30), Leandro Damião (D'Alessandro 67)
Milan: Abbiati (Roma 46); Zambrotta (Oddo 78), Thiago Silva, Yepes, Antonini; Gattuso (Valoti 66), Ambrosini (Emanuelson 78), Seedorf; Robinho (Boateng 66); Pato, Ibrahimovic (Cassano 66)
Betting on Serie A? Bet365 are offering a 100% deposit bonus, up to £200 - find out more