A Look at Liverpool's 4 most recent European Round of 16 ties

In recent years, we haven’t seen Liverpool in Europa League play all that often, but the Reds in a European Round of 16 knockout tie is a very familiar sight. This is the seventh straight year in which they’ve reached at least that stage of a European contest, a feat they’ve accomplished in all but one season of the Klopp era. 

Let’s take a look at what Liverpool has been able to accomplish in each of their past four trips to the Round of 16.

2022-23 UCL - Real Madrid

Once again, Liverpool’s favorite competition ended up with a matchup against their least-favorite opponents.

Truth be told, last season was probably not the year to secure that seventh European Cup given the club’s injury woes, but a first-round knockout draw with Carlo Ancelotti’s Real Madrid was an instant death sentence. 

At first, it looked like Liverpool were flying away with the win for once. A rare Thibaut Courtois gaffe and a pair of early goals granted the Reds a 2-0 Anfield lead after just 14 minutes.

Of course, the win was not meant to be. Alisson contributed an uncharacteristic mistake of his own, but that was far from the only issue as Madrid stormed back with five unanswered goals. It turned into a rout for the ages, and Madrid capped things off with an easy 1-0 home win in the second leg to move on to the Quarterfinals. 

2021-22 UCL - Inter Milan

This season would end with another crushing loss to Madrid, but the Round of 16 was certainly a fun one.

It was a tense first half against Inter Milan at the San Siro, but in a flurry of activity, Roberto Firmino opened the scoring with a 75th minute strike, while Mo Salah added on just eight minutes later.

The Anfield leg was a rather routine one, as Liverpool were quite happy to dominate possession without creating much danger. A lovely strike from Lautaro Martinez made the game a bit interesting with just under a half hour to go, but Alexis Sánchez was sent off a minute later after receiving his second yellow card.

The Reds lived to fight another day, and moved on to the quarterfinal. Incidentally, this turned out to be a matchup between UCL runners-up from the 2022 and 2023 finals, as Inter would suffer a similar fate just the next season. 

2020-21 UCL - RB Leipzig

Despite a largely injured XI in late 2021, Liverpool were able to get by RB Leipzig with relative ease in the Round of 16. The two legs were profoundly similar; both featured a Salah opener in the second half, with Mané following up with a goal of his own within the next five minutes. 

The one wrinkle with this tie was the lingering effect of the COVID-19 pandemic. Thankfully, both legs were able to be played as scheduled in terms of timing, but both were played at Puskás Aréna in Budapest, Hungary, due to travel restrictions between Germany and the U.K. 

2019-20 UCL - Atletico Madrid

Here’s a not-so-fun fact; Klopp’s Liverpool are 0-5 against Madrid teams in UCL knockout situations, and 11-0 against everyone else.

This matchup was a strange one, as it came just at the beginning of the COVID-19 outbreak, and it signaled a premature end to Liverpool’s title defense in the wake of their glorious 2019 triumph.

The first leg in Madrid saw a quick Atletico goal, followed by nearly a full 90 minutes of parking the bus to prevent Liverpool from securing an all-important away goal.

The Reds struck first at home through Gini Wijnaldum, but that was all they’d get in regulation- with the aggregate at 1-1 and no away goals scored, it was time for extra time. 

Roberto Firmino quickly fired Liverpool in front, but Marcos Llorente equalized for Atleti, which put them in position to lead given the ridiculous away goals rule. Liverpool threw the team forward, which led to an astonishing two more Atleti goals, including another from Llorente.

The sting was greatly softened by the team’s historic first Premier League title, but nonetheless, this unceremonious end to the team’s European campaign has to go down as one of the worst attempts at a title defense in recent memory. 

Bonus: 2015-16 Europa League - Manchester United

Liverpool’s last Europa League run also featured the club’s first taste of Klopp magic, as their new manager, appointed that October, led them to the competition’s final, through a highly theatrical path.

The Reds slipped through the Round of 32 by a 1-0 aggregate, and would later dispatch Klopp’s former club, Borussia Dortmund, in an incredibly dramatic tie, but before that, they had to get past bitter rivals Manchester United.

The first leg was a thumping 2-0 Anfield victory, featuring a penalty kick scored by Daniel Sturridge and a dagger of a 73rd-minute strike from Roberto Firmino.

Back in Manchester, Anthony Martial made the second leg a bit interesting with a penalty goal of his own, before Philippe Coutinho iced the victory with an all-important away goal to put Liverpool up 3-1 on aggregate.