Europa League last 16 draw: Best and worst-case scenarios for Liverpool

Jurgen Klopp's men progressed as Group E winners at the end of 2023, despite two rocky trips to Toulouse and Union SG which ended in defeat.

That allowed them to sit back and watch on as 16 sides battled it out in the playoffs for the remaining eight places in the next round over the last two weeks.

The eight ties which decided who advanced pitted the clubs which dropped down from the Champions League against those who finished as runners-up across the Europa League group stage.

With some European heavyweights in UEFA's second-tier competition, and a few relative minnows looking at a rare shot at glory on the continent, Sports Mole looks at the best and worst-case scenario for Liverpool heading into the draw.

Best-case scenario: Qarabag FK

There are some sides on the unseeded half of the draw currently in the midst of unconvincing runs of form and crises behind the scenes, namely Marseille, while the likes of Sparta Prague and Freiburg are inexperienced when it comes to recent history in Europe.

There is one club left in the Europa League that has never ventured this far before though, and became their nation's first ever representative in a UEFA last 16 draw.

That club is Qarabag of Azerbaijan, who overcame Braga in remarkable circumstances on Thursday evening.

After going 4-1 up away in Portugal in the first leg, the Azeri side may have thought the job was almost done, but a late penalty at the Quarry meant they took just a two-goal lead back to Baku.

A second-half red card to Elvin Cafarquliyev blew the tie wide open, and Braga netted twice late on to force extra time, making them huge favourites in the additional 30 minutes given their man advantage.

However, Qurban Qurbanov's side showed incredible courage to retake the lead thanks to Matheus Silva's strike shortly after the 100-minute mark, and even a Simon Banza penalty to level the tie up again did not dampen their spirits, as teenager Nariman Akhundzade won the tie for Qarabag in the 122nd minute.

Scoring two goals in extra time with 10 men to win 6-5 on aggregate was undoubtedly the story of the night in the Europa and Europa Conference League, and there will be a refreshing new name in the last 16 of this competition.

However, there is no doubting their limitations, and a club as big as Liverpool, in a league as resource-rich as the Premier League, will have little trouble in progressing should they be paired with Azeri minnows, despite the lengthy trip the Reds will have to make venturing towards the Asian continent.

Qarabag have faced English sides on six previous occasions, losing each time, home and away to Tottenham Hotspur in 2015, Chelsea in 2017 and Arsenal in 2018.

The results against Chelsea were most damning, as they lost by an aggregate score of 10-0 across their two Champions League group stage encounters.

Qarabag's current crop of players also showed their shortcomings when facing the might of Bayer Leverkusen under Xabi Alonso, losing 5-1 at the BayArena in the group stage this season.

Their finest result to date came in holding Atletico Madrid to a 1-1 draw at the Metropolitano back in 2017, but home and away defeats are likely should they face Liverpool here.

Worst-case scenario: AC Milan

While Liverpool will fancy their chances against almost any side in Europe, given their successes on the continent under Klopp, any club will be wary when facing a team as illustrious as AC Milan.

The seven-time Champions League winners dropped out of that competition in the group stage, after finishing third in the group of death behind Borussia Dortmund and Paris Saint-Germain.

Milan took their prospects of qualifying out of that group into the final matchday, but despite beating another English side in the form of Newcastle United, that was ultimately only enough for third, and a spot in the Europa League.

Stefano Pioli's side were handed a tough draw though, as their opponents Rennes had hit a run of form that not many sides across Europe's top five leagues could match.

However, a dominant first-leg performance saw the Rossoneri blow their French counterparts away winning 3-0 at San Siro, meaning a 3-2 defeat in the second leg meant little in the context of the tie.

While it has been 17 years since their last success on the continent (against Liverpool in the 2007 Champions League final), Milan came close to replicating past successes in that competition last season.

It was their cross-city rivals Inter Milan who ended their dreams in devastating fashion in the semi-finals though, but Pioli's men are one of the favourites in the Europa League this season, along with Liverpool and Leverkusen.

Liverpool and Milan have a very well documented history, as their meeting in the 2005 Champions League final has gone down in the history books as one of the most remarkable comebacks in the history of the sport.

Despite being 3-0 down, Liverpool fought back to force penalties, where they defeated Milan to clinch a fifth title, but the Italians would get their revenge two years later in Athens.

In more recent times, Liverpool completed a home and away double over Milan in the 2021-22 Champions League group stages, winning 3-2 at Anfield and 2-1 in Italy, but Liverpool will have to take the Milan challenge very seriously, with the Rossoneri also performing well in Serie A.

EUROPA LEAGUE LAST 16 POTS

Seeded:

Liverpool (ENG)

Brighton & Hove Albion (ENG)

West Ham United (ENG)

Rangers (SCO)

Atalanta BC (ITA)

Villarreal (ESP)

Bayer Leverkusen (GER)

Slavia Prague (CZE)

Unseeded:

AC Milan (ITA)

Benfica (POR)

Sporting Lisbon (POR)

Roma (ITA)

Marseille (FRA)

Freiburg (GER)

Sparta Prague (CZE)

Qarabag (AZE)