Europa League knockout play-off: AC Milan cling on to last 16 place; Qarabag make history

  • AC Milan lost their second leg against Rennes but advanced anyway
  • Qarabag won in dramatic fashion to make history for Azerbaijani football
  • Marseille, Benfica & Roma also through; Galatasaray out

Qarabag are going where no team from Azerbaijan has been
Qarabag are going where no team from Azerbaijan has been / Anadolu/GettyImages

AC Milan have a 3-0 first leg win to thank for their place in this season's Europa League last 16 draw, having fallen to a 3-2 defeat in the return game with Rennes in France.

Benjamin Bourigeaud struck a hat-trick for the home side, including two second half penalties that restored some pride but will only be consolation in reality. The midfielder put Rennes ahead twice, cancelled out first by Luka Jovic and later Rafael Leao, before his third won in on the night.

Qarabag have been flying the flag for Azerbaijani football for years and made more history by becoming the first club from the country to reach the last 16 of a UEFA competition.

They were actually beaten by Braga on the night in Baku after being reduced to ten players shortly before the hour mark when Elvin Cafarguliyev was sent off. At that stage, Qarabag still led 4-2 on aggregate, but Roger Fernandes and Alvaro Djalo erased that cushion to force extra-time. Yet Qarabag rallied to retake the lead through Matheus Silva, before Simon Banza’s penalty for Braga looked like it might force a shootout. Incredibly, teenage talent Nariman Akhunzade won it for the ten men in the 122nd minute of the game.

Roma kept their hopes of avenging last season's final defeat and winning a second European trophy in the space of three years continued after going the distance with Feyenoord. A 1-1 draw over 90 minutes followed on from a 1-1 tie in the first leg, with the teams not able to be separated by a further half hour in extra-time. A shootout followed, with Romelu Lukaku missing for Roma, but David Hancko and Alireza Jahanbaksh also failing to score for Feyenoord. By the time, Nicola Zalewski converted Roma's fifth to make it 4-2, the deficit was too large for Feyenoord to claw it back.

Joining them in the next round is Marseille after initially going a goal down against Shakhtar Donetsk at Stade Velodrome. Pierre-Emerick Aubameyang, Ismaila Sarr and Geoffrey Kondogbia were all on the score-sheet after Shakhtar’s early penalty from Heorhiy Sudakov.

Sporting CP had done their hard work in the first leg to lead 3-0 on aggregate over Young Boys coming into this week’s game and did enough to keep their advantage. Viktor Gyokeres actually extended the lead with an early strike, with Silvere Ganvoula M’boussy’s late reply for the Swiss side only good enough to even things up on the night.

Sparta Prague successfully overturned a first leg defeat against Champions League dropouts Galatasaray. The tie was ultimately decided by late goals after Kaan Ayhan’s 70th minute red card for Gala, who led 4-3 on aggregate at that point after early strikes had been exchanged.

Sparta made their man advantage count to the fullest, with Indrit Tuci and Lukas Haraslin taking them from 4-3 down on aggregate to 5-4 ahead.  With Galatasaray throwing everything at it, Jan Kutcha’s breakaway goal at the other end deep into stoppage time sealed it.

It was all to play for between Freiburg and Lens after a stalemate first leg a week ago. And while fans in France had been starved of a goal, those watching the second leg in Germany got five.

Remarkably, Lens were on the brink of going through, having led 2-0 at half-time through David Costa and Elye Wahi. Even as the reached the end of the 90 they still led 2-1, only for a stoppage time surge from Freiburg as Roland Sallai pulled his team level in the 92nd minute. It was left for Michael Gregoritsch to tip the tie in favour of Freiburg in the first half of extra-time.

There was nothing to separate Toulouse and Benfica in France, with the latter’s 2-1 aggregate lead from the first leg in Portugal last week deciding things.

The eight winners from this round now go forward to Friday's last 16 draw, where each one will be paired with a seeded team, all of whom were group winners and bypassed the play-off.

Europa League knockout play-off second leg results


Qarabag 2-3 Braga (Agg. 6-5)

Rennes 3-2 AC Milan (Agg. 3-5)

Freiburg 3-2 (aet) Lens (Agg. 3-2)

Toulouse 0-0 Benfica (Agg. 1-2)

Marseille 3-1 Shakhtar Donetsk (Agg. 5-3)

Roma 1-1 Feyenoord (Agg. 2-2) (Roma win 4-2 on penalties)

Sparta Prague 4-1 Galatasaray (Agg. 6-4)

Sporting CP 1-1 Young Boys (Agg. 4-2)

2023/24 Europa League last 16 qualified teams




West Ham United

Group A winner


Brighton & Hove Albion

Group B winner



Group C winner



Group D winner



Group E winner



Group F winner


Slavia Prague

Group G winner


Bayer Leverkusen

Group H winner



Knockout play-off winner


AC Milan

Knockout play-off winner



Knockout play-off winner



Knockout play-off winner



Knockout play-off winner



Knockout play-off winner


Sparta Prague

Knockout play-off winner


Sporting CP

Knockout play-off winner