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Champions League round of 16: The previous meetings

After a break of over three months, Europe’s biggest club competition is back on our screens this week.

There’s plenty to look forward to in the coming days. Paris Saint-Germain and Bayern Munich face each other in the standout tie of the round, while we’ve also got a repeat of last year’s final on the way.

It’s tough to call who will make it to the quarter-finals, but maybe history can give us an indication. Here are the previous meetings from the Champions League round of 16 ties.

AC Milan vs Tottenham Hotspur

This week, AC Milan will face Tottenham Hotspur for just the third time ever. The first two fixtures came almost 12 years ago to the day, and it was the latter who came out on top.

In a first leg that was best remembered for a fiery clash between Gennaro Gattuso and Spurs coach Joe Jordan, the visitors claimed a 1-0 victory at the San Siro thanks to Peter Crouch’s late goal.

The Rossoneri came close to levelling the scores numerous times in the reverse fixture but could not find a way past an inspired Heurelho Gomes in the Tottenham goal.

Paris Saint-Germain vs Bayern Munich


For these two sides, this competition has added importance. Having already won everything domestically several times over, an early exit in the Champions League can be the difference between a good season and a bad one.

The pair have met on 11 occasions, most notably in the 2020 final. In that instance, Bayern Munich took the crown, thanks to Kingsley Coman’s header in the second half.

PSG got some form of revenge the following year, eliminating the Bavarians in the quarter-finals in a thrilling tie. Kylian Mbappe was at his best in the first leg, scoring twice as his side took a 3-2 lead back to the Parc des Princes.

Eric Maxim Choupo-Moting pulled one back in the second leg, but this wasn’t enough to prevent his side from being eliminated on away goals.

For the highest-scoring clash between these two, you have to go back to the group stages of 1997. Bayern pulled off a resounding 5-1 victory, with braces from Giovane Elber and Carsten Jancker.

Borussia Dortmund vs Chelsea

Despite being two of only 22 sides to have won this competition, Borussia Dortmund and Chelsea have never faced each other.

In the last ten seasons, Chelsea have played nine fixtures against German opposition, winning three, drawing four and losing two. The most recent meeting came with Bayern Munich in the round of 16 in 2020, which they lost 7-1 on aggregate.

Borussia Dortmund’s record against English teams isn’t particularly favourable either. You have to go back to 2016 for the last time they won against a Premier League side, beating Tottenham at White Hart Lane. Since then, they have played ten games against English clubs, drawing two and losing eight.

Club Brugge vs Benfica

Once again, this is the first time that these two teams will meet.

Club Brugge were drawn against second-placed Liga Portugal side Porto in the group stages, with varying results. In the away fixture, they cruised to a 4-0 win. In the home game, however, they lost by the same scoreline.

Benfica’s last trip to Belgium came in the Europa League group stages in 2020, when they faced Standard Liege. They took four points from the two games, winning 3-0 at home and drawing 2-2 in the reverse fixture.

Eintracht Frankfurt vs Napoli

Napoli were the top scorers in the group stages, bagging 20 goals in their six outings. This will give them hope of notching their first-ever goal against Eintracht Frankfurt.

These two have met twice before, coming in the third round of the UEFA Cup in the 1994/95 season. Both games finished 1-0 to Frankfurt, with Tony Yeboah and Ralf Falkenmayer scoring.

Liverpool vs Real Madrid

As two of the most successful clubs in the history of European football, it will come as little surprise that Liverpool and Real Madrid have faced each other often. They’ve clashed in three finals, making it the most common final fixture.

In recent years, Los Blancos have got the better of their opponents. They lifted the trophy against them last season, thanks to Vinicius Junior’s second-half goal and a brilliant Thibaut Courtois performance.

And four years earlier, they also defeated the Reds in the final. This time, it was a mix of Gareth Bale magic and Loris Karius calamity, as the game ended 3-1 to Madrid.

But Liverpool have had some joy against the Spanish giants. The third of their six European titles came against the La Liga side, winning 1-0 in the 1981 European Cup final following Alan Kennedy’s late finish.

Porto vs Inter Milan

It’s been a while since Porto and Inter Milan were drawn against each other. Their last meeting came in the group stages in 2005, with both sides winning one game each – Inter would later top the group, while Porto finished bottom.

The only other clashes came in the previous season, and it was the Nerazzurri who emerged victorious over the two legs. The first game finished as a 1-1 draw, but a hat-trick by Adriano at the San Siro was enough to take Inter to the quarter-finals.

Manchester City vs RB Leipzig

For the second year in a row, Manchester City and RB Leipzig will face off. If the games are anything like last year’s meetings, we could be in for a treat.

The first match – and the first-ever meeting between these two – came at the Etihad Stadium in last season’s group stage.

Despite Christopher Nkunku’s hat-trick for the visitors, the Cityzens pulled off a resounding 6-3 victory, with the likes of Riyad Mahrez, Jack Grealish and Gabriel Jesus among the scorers.

But the reverse fixture belonged to Leipzig, as they won 2-1. Dominik Szoboszlai and Andre Silva were on target for the Die Roten Bullen, while Mahrez grabbed one for the away side.

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