AC Milan scored a 120th-minute equaliser and then came out on top in a 24-penalty shootout to beat Rio Ave and reach the Europa League group stage.
Trailing 2-1 in the final seconds of extra time the visitors were awarded a penalty, which Hakan Calhanoglu converted.
That took the game to a shootout, with Milan coming out on top 9-8 in the 12th round of spot-kicks.
The win means AC Milan will go into Fridayβs group-stage draw.
Who said you could go to bed before watching this ‡οΈ
Qualcuno pensava di andare a dormire senza rivedersi la serie π
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dei calci di rigore? ‡οΈ#RioAveMilan #UEL #SempreMilan pic.twitter.com/TDJABBrFzV
β AC Milan (@acmilan) October 1, 2020