Liverpool's manager Jurgen Klopp will be eager to leave on a high as the Reds are chasing a quadruple titles this season. Image Credit: AFP

Nyon: Three-time winners Liverpool were drawn to face Sparta Prague in the Europa League last 16 on Friday, while unbeaten Bundesliga leaders Bayer Leverkusen will take on Azeris Qarabag.

Jurgen Klopp’s Liverpool will be strong favourites to reach the quarter-finals as they bid for a quadruple in the German’s final season before stepping down as manager.

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The first leg will be played in the Czech capital on March 7, with Anfield hosting the return game a week later.

Leverkusen, led by Xabi Alonso, are unbeaten in 32 matches in all competitions this season, and will again face Qarabag, having already seen off the Azeri champions twice in the group stage.

Also renewing acquaintances will be last year’s Europa Conference League winners West Ham and Freiburg, after David Moyes’ side’s brace of victories against the Bundesliga club in Group A.

Last-16 draw
Sparta Prague (CZE) v Liverpool (ENG)
Marseille (FRA) v Villarreal (ESP)
Roma (ITA) v Brighton (ENG)
Benfica (POR) v Rangers (SCO)
Freiburg (GER) v West Ham (ENG)
Sporting Lisbon (POR) v Atalanta (ITA)
AC Milan (ITA) v Slavia Prague (CZE)
Qarabag (AZE) v Bayer Leverkusen (GER)
— First legs to be played on March 7, second legs to be played on March 14.

Milan overcome spirited Rennes

Seven-time European champions AC Milan continue their bid to win a maiden Europa League title against Slavia Prague after their knockout round play-off win over Rennes.

Scottish Premiership leaders Rangers, losing finalists in 2022, take on Portuguese Primeira Liga pacesetters Benfica, still chasing a first European trophy since 1962.

Premier League club Brighton continue their first ever European adventure at last season’s runners-up Roma.

AC Milan overcame a spirited Rennes 5-3 on aggregate despite a 3-2 loss in Thursday’s play-off second leg, where they were joined by fellow former European champions Benfica and Marseille.

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Rennes' Amine Gouiri (centre) vies with Theo Hernandez on Thursday. Image Credit: AFP

Benjamin Bourigeaud scored a hat-trick for Rennes, including a pair of penalties, but goals from Luka Jovic and Rafael Leao ensured Milan were never really in danger of blowing a 3-0 lead from the first leg.

Benfica also saw off French opposition as a 0-0 draw away to Toulouse was enough to send the Portuguese side through following their 2-1 victory in last week’s first leg in Lisbon.

Goalless opening leg

Lens, who dropped down from the Champions League into the knockout play-off round, became the third French club to go out after Freiburg fought back from two goals down to win 3-2 after extra time.

David Pereira da Costa and Elye Wahi put Lens in control of the tie following a goalless opening leg, but Roland Sallai struck twice to force extra time in Germany.

Michael Gregoritsch grabbed the winner in the 99th minute for Freiburg.

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Benfica's Joao Neves celebrates after the match against Toulouse. Image Credit: Reuters

Marseille kept French interest in the competition alive as they rallied to beat Shakhtar Donetsk 5-3 on aggregate after a 3-1 victory at the Velodrome.

Georgiy Sudakov stroked home a penalty early in Marseille before the hosts replied via Pierre-Emerick Aubameyang’s record-setting 31st Europa League goal.

Two-goal advantage

Ismailia Sarr fired Marseille ahead on 74 minutes and Geoffrey Kondogbia added a late third on Jean-Louis Gasset’s debut as coach after the departure of Gennaro Gattuso.

Qarabag, 4-2 winners last week away to Braga, blew a two-goal advantage after being reduced to 10 men as their Portuguese opponents took the tie to extra time.

The Azerbaijani team went back in front through Matheus Silva but it looked destined for penalties when Simon Banza’s penalty made it 3-1 on the night to Braga.

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Marseille's Pierre-Emerick Aubameyang celebrates after scoring his team's first goal against Shakhtar Donetsk. Image Credit: AFP

Nariman Akhundzade sent Qarabag into the next round though with a goal in the 122nd minute.

Sporting progressed 4-2 on aggregate despite a 1-1 draw at home to Swiss champions Young Boys. Sparta Prague overturned a 3-2 first-leg deficit by scoring three times after Galatasaray’s Kaan Ayhan saw red to win the return fixture 4-1.

Ajax scrap to win

Ajax scraped past Norwegian champions Bodo/Glimt after extra time to reach the Europa Conference League last 16.

After a 2-2 draw in Amsterdam, the Dutch giants went ahead when Steven Berghuis struck in first half of the second leg.

But they had centre-back Josip Sutalo sent off early in the second half and Patrick Berg’s equaliser took it into extra time, with Kenneth Taylor’s 114th-minute effort putting Ajax through 4-3 on aggregate.

Dinamo Zagreb knocked out Real Betis 2-1 on aggregate and Union Saint-Gilloise of Belgium took down 2022 Europa League winners Eintracht Frankfurt 4-3 over two legs.

Olympiakos also moved on along with Swiss side Servette, Norwegians Molde and Austria’s Sturm Graz.