AC Milan advanced to the round of 16 in the Europa League despite a 3-2 loss at Rennes in the second leg of their playoff on Thursday.
Milan, which won 3-0 at the San Siro last week, eliminated its French opponent on a 5-3 aggregate score.
The Italian powerhouse, a seven-time European champion, has never won the second-tier Europa League or its predecessor, the UEFA Cup.
Midfielder Benjamin Bourigeaud's hat trick put the hosts up three times with Milan quickly answering twice.
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Bourigeaud netted the opener in the 11th minute with a fierce right-footed shot from over 20 meters to beat goalkeeper Mike Maignan.
Forward Luka Jovic canceled it out 10 minutes later with a header off a cross by captain Theo Hernandez.
Bourigeaud made it 2-1 early in the second from the penalty spot but Rafael Leao equalized after four minutes on a fine solo effort.
Bourigeaud sent Maignan the wrong way with another spot kick to make it 3-2.
The eight runners-up in the Europa League group stage played the eight third-place teams from the Champions League group stage in the playoffs.
The eight winners will take on the Europa League's group winners, who qualified directly for the round of 16. They are Liverpool, West Ham and Brighton from the Premier League, as well Leverkusen, Atalanta, Villarreal, Rangers and Slavia Prague.
The draw is scheduled for Friday.
Two-time European champion Benfica held host Toulouse 0-0 to progress 2-1 on aggregate.
EUROPA CONFERENCE LEAGUE
In the third-tier competition, Takuro Kaneko's second-half equalizer salvaged a 1-1 draw for Dinamo Zagreb and secured a spot in the next round at the expense of Real Betis after the Croatian team upset the Spanish favorite 1-0 in the opening leg in Sevilla.
Servette's lone goal at Ludogorets was enough to advance after a 0-0 draw in the first leg.
In Wednesday's game, Maccabi Haifa drew 1-1 at Gent to advance.
The competition's playoffs features the runner-up teams from the group stage facing the third-place finishers in the Europa League group stage. The eight group winners, including Aston Villa and last year's runner-up Fiorentina, have advanced to the last 16.