Football News

Grudge matches and favourite opponents for each remaining Champions League quarter-finalist

By Ben Green

Published: 13:00, 16 March 2023

If recent events have taught us anything, it’s that Pep Guardiola resembles a deer caught in the headlights away to Tottenham.

Of course, Guardiola is not the only manager to have his own kryptonite, a ‘bogey’, team — or, in his case, a venue — they just can’t seem to shake. And it’s certainly not a phenomenon exclusive to the domestic circuit. Just ask Bayern Munich fans for their thoughts on AC Milan.

Speaking of which, the Bavarians could once again test themselves against the Rossoneri. But, who is the nightmare opponent of every quarter-final club, and who are their hoping to draw given their past successes?

For those still standing in this season’s Champions League, we requested Stats Perform data revealing just that. Or, more specifically, the team with the best win rate against every remaining contender in the modern era (since the competition’s 1992 rebranding).


Favourite opponent: When it comes to facing those remaining in the 2022/23 tournament, Benfica don’t possess a single winning record. Their best series of performances have come against Milan, who they’ve met on four previous occasions. Even so, the Eagles are yet to enjoy a win over the seven-time European champions, a goalless stalemate at home in the 1994/95 quarter-finals was followed up by a 1-1 group stage draw in Lisbon more than a decade later. Milan won each reverse fixture at the San Siro (2-0 in March 1995 and 2-1 in September 2007).

Grudge match: It’s no surprise to see a club of Bayern Munich’s stature and pedigree crop up on this list and be the thorn in the side of a club in Europe. The Bavarians have played Benfica six times in the competition and only failed to win once. That came in the 2015/16 quarter-finals, with Rui Vitoria putting together a commendable 2-2 draw against Pep Guardiola’s side. To their credit, the Lisbon club only marginally lost the first leg 1-0. But since then, it’s been one-way traffic. The two proceeding home ties for Bayern have seen them win 5-1 (2018/19 groups) and 5-2 (2021/22 groups), with Robert Lewandowski netting a hat-trick in the latter.


Favourite opponent: Graham Potter’s men will be hoping for another Lisbon trip as Chelsea in the past have claimed a 3-1 quarter-final aggerate success over Benfica who happens to be one of many sides, including Milan, they’ve never tasted defeat against. During that 2011/12 campaign, which ended in winning their first-ever European Cup, the likes of Frank Lampard, Salomon Kalou and Raúl Meireles would all get on the scoresheet against Portugal’s best.

Grudge match: Of the sides remaining in this season’s competition, it’s Inter who Chelsea have never managed to get the better of. They’ve only met twice before in 2010 when the Italians were led by former Blues head coach Jose Mourinho; a 2-1 win in Milan was followed by a 0-1 success at Stamford Bridge. Their last-16 success would further the groundwork en route to an inevitable European Cup success. Diego Milito, Esteban Cambiasso and Samuel Eto’o would all breach Chelsea’s goal. Didier Drogba infamously got himself sent off in the dying stages of the Stamford Bridge second leg.

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Bayern Munich

Favourite opponent: There’s a growing theme here. Given they play their football outside Europe’s big five leagues, meaning they’re consistently losing their major stars, Benfica are often the underdogs when playing in European football’s premier competition. It comes as no surprise to find that Bayern has enjoyed their meetings with the Eagles, winning five of six previous showdowns, while being held once. Just two of those games have come outside the group stages. During the 2015/16 campaign Bayern would run out 1-0 winners at home before playing out a 2-2 draw in the following leg. On that day Arturo Vidal and Thomas Müller put the visitors in front after Raúl Jiménez opened the scoring. Talisca would net a late free-kick to keep things interesting.

Grudge match: Milan are European royalty, a notion reinforced by their bulging trophy cabinet and their stellar record against Bayern Munich. A powerhouse themselves, the German giants have faced the Rossoneri on six occasions in the Champions League, and failed to produce a single win in any of those games. Between 2002 and 2007, Carlo Ancelotti outfoxed and outmanoeuvred Ottmar Hitzfeld in the groups (2002/03), the last 16 (2005/06) and the quarter-finals (2006/07). Put some respect on the ‘Diva Whisperer’s’ name.

Inter Milan

Favourite opponent: Inter are one of a few teams with a 100% record against Chelsea and if the first reunion was dominated by Mourinho’s ‘homecoming’, then a future meeting this season will undoubtedly revolve around much-maligned Belgian marksman Romelu Lukaku, who is back at Inter (albeit only on loan from the Premier League giants).

Grudge match: No club can hold a candle to Real Madrid’s dominance in the Champions League, which naturally means the record-holders have a stranglehold over a few clubs. Inter are one of those, with the pre-eminent Spanish giants claiming five wins in their six showdowns against the Nerazzurri. Despite this fixture involving two behemoths, they’ve only ever met in the groups. In 1998/99, Guus Hiddink claimed one victory over Luigi Simoni, before feeling the wrath of Ronaldo and Co at the San Siro. Since then, though, it’s been a clean sweep, with both Antonio Conte and Simone Inzaghi proving powerless to placate the Galactico might.

Manchester City

Favourite opponent: Of the remaining sides in this season’s Champions League knockout round, Manchester City have won half of their previous battles against Bayern Munich (three wins and three losses) and Napoli (two wins and one loss) but you would be hardpressed to say the defending Premier League champions will hope to face either of them in the quarter-finals this time.

Grudge match: City are still looking for that elusive first European Cup and they’ve come really close. Pep Guardiola, a two-time winning manager at Barcelona, must have felt a third winners medal was coming his way in the most recent all-Premier League final. However, the spoils went to Chelsea, and when presiding over their record against teams left in the competition it’s the Blues who are unbeaten against English football’s current kings.


Favourite opponent: Milan v Bayern is a European clash of giants and when considering their domineering past it shouldn’t be surprising to learn that it’s the Rossoneri who dominates the head-to-head standings. However, the most recent of their six meetings came in the 2006/07 quarter-finals, when Milan ran out 0-2 winners in Munich which came on the back of a 2-2 first-leg draw. Even crazier is the fact their first-ever showdown came in October 2002 when Filippo Inzaghi netted a brace in a 1-2 win at the old Olympiastadion München.

Grudge match: From those remaining in the 2022/23 tournament, it’s Chelsea who Milan have found hard to crack. They’ve met on four previous occasions with two of those outings ending in stalemate while the Premier League side triumphed in the other two showdowns. However, none of those past matches has come in the knockout rounds.



Favourite opponent: Guess who? It’s Benfica again. Napoli, unlike their fellow quarter-finalists, don’t have a stellar European Cup past, they sit alongside Man City as the only non-winners left in the competition, so there’s not much to go when delving into their individual records against clubs. But they have faced Benfica twice, winning both matches, those games took place during the 2016/17 group stage with Dries Mertens finding the net on three occasions.

Grudge match: In the early days of the Sheikh Mansour era when City were still a Champions League start-up trying to find their feet in a sea of giants, they actually failed to beat Napoli twice in the 2011/12 groups, with Edinson Cavani netting a brace in a 2-1 win in Campania. Fast forward six years to 2017 and the club are a more experienced beast with Guardiola at the helm. They won both fixtures in Group F of that 2017/18 season, which has incidentally made them Napoli’s European kryptonite.

Real Madrid

Favourite opponent: Real Madrid’s second-ever European Cup final defeat came at the hands of Inter Milan, but in the Champions League era the Nerazzurri have been on the receiving end of some disappointing losses, the sole exception coming in November 1998 when Roberto Baggio inspired Inter to a famous 3-1 win. Since then Real have faced Inter on four occasions winning each time including during last season’s group phase.

Grudge match: Real are a magnet for success and appear almost impervious to disappointment, but they have proven soft-centred at times, with two clubs enjoying ‘bogey team’ status against them. One of them is Chelsea, who hold a very palatable record against them, something Liverpool fans can only look upon with envy.

Thomas Tuchel famously won 3-1 on aggregate in the 2020/21 semi-finals en route to European domination, while their second showdown is slightly more conflicting. Real ultimately went through on aggregate in their quarter-final showdown last season, but Chelsea ‘technically’ have a win on the board from the second leg.

CSKA Moscow have a near-identical record against Real Madrid (P4W2D1L1) but have scored one goal fewer than Chelsea against them.