Familiar foes Real Madrid and Manchester City will go toe-to-toe in the Uefa Champions once again this week with the two teams clashing at the Bernabeu on Wednesday.

Remarkably, the last-16 first leg in Spain will be the 12th game between the two clubs this decade, the last of which only taking place three months ago.

That league-phase match ended in a 2-1 win for City despite falling behind in the 28th minute to a Rodrygo goal. But Nico O’Reilly and an Erling Haaland penalty just before the break would secure victory for the English club.

Xabi Alonso has since been sacked as Real manager with Alvaro Arbeloa taking over in January. City and Madrid sit second in the Premier League and La Liga, respectively.

Below, we take a look back at all the matches between the duo since 2020.

2019/20

Last 16 – Man City win 4-2 on aggregate

City secured their quarter-final spot by winning both legs 2-1. The first, in Madrid, saw Pep Guardiola’s side produce a spectacular comeback after Isco had put the home side ahead on the hour after a defensive mix-up by Rodri and Nicolas Otamendi.

Gabriel Jesus nodded City level before a Kevin de Bruyne penalty would flip the match on its head. Sergio Ramos was also shown a late red card, completing a disappointing night for Zinedine Zidane’s Los Blancos.

Back at the Etihad, Raheem Sterling’s 100th City goal put his team into an early lead only for a Karim Benzema header to make it 1-1 just before the half-hour mark. But Real hopes were ended in the 68th minute when Rafael Varane’s misjudged header allowed Gabriel Jesus in on goal and the Brazilian finished from a tight angle.

City manager Guardiola said: “We are here to try and win the Champions League. It is one step, if we think that is enough we will show how small we are. If you want to win you have to beat the big clubs.”

City’s hopes of a first European Cup crown were ended in the next round, though, when they fell to a surprise 3-1 home loss to French side Lyon in the last-eight mini tournament held in Lisbon that was delayed until August due to Covid-19.

2021/22

Semi-finals – Real win 6-5 on aggregate after extra-time

A sensational couple of matches ended with eventual winners sealing a breathless victory at the Bernabeu. City had made a flying start to the first leg with De Bruyne and Jesus putting them 2-0 up within 11 minutes before Benzema gave Real a lifeline after 33 minutes.

Phil Foden restored City’s two-goal advantage just after half-time only for Vinicius Junior to score a superb solo second for Real two minutes later. Bernardo Silva fired into the top corner for City before Benzema completed an astonishing game by sending a Panenka penalty past Ederson, puling the score back to 4-3.

Incredibly, the drama would ramp up even further in Spain. The tie looked over when Riyad Mahrez made it 5-3 on aggregate in the 73rd minute. But a quickfire Rodrygo double – in the 90th and 91st minutes – sent the game into extra-time when a Benzema penalty would seal Real’s final spot.

Real manager Carlo Ancelotti said: “I cannot say we are used to living this kind if life, but what happened tonight it happened against Chelsea and also against PSG [in the previous rounds]. If you have to say why, it is the history of this club that helps us to keep going when it seems that we are gone.”

Real would go on to beat another English club in the final when a Vinicius Junior goal sealed a 1-0 win over Liverpool and the club a 14th European Cup.

2022/23

Semi-finals – Man City win 5-1 on aggregate

This was the season where Guardiola finally guided City to Champions League glory.

A goal in each half from Vinicius and then De Bruyne in Madrid meant the tie went to Manchester with the tie on a knife-edge, but a relentless attacking display at the Etihad would blow away the reigning champions.

A first-half double from Silva had put City firmly in control until a deflected Manuel Akanji header made it 3-0 14 minutes from time. Substitute Julian Alvarez completed the rout in stoppage time.

City manager Guardiola said: “When the draw was Madrid, I said, ‘Yeah, I want it’. After 10 or 15 minutes, I was feeling all the pain that we had [with] what happened last season. It was really tough, losing the way we lost and I think in the moment we had to swallow poison. But during one year we showed how special a group of players these are.”

In the final, a 68th-minute strike from Rodri would earn City a 1-0 win over Inter Milan and their first Champions League crown as well as a trophy treble that campaign.

2023/24

Quarter-finals – Real win on penalties

Another remarkable tie would this time see Real come out on top. The first leg at the Bernabeu saw Silva score after two minutes with a clever free-kick before Real took control through deflected strikes from Eduardo Camavinga and Rodrygo – with the former going down as an own goal against Ruben Dias.

Goals from City’s Foden and Josko Gvardiol flipped the script again only for Federico Valverde’s brilliant volley to bring the scores level at 3-3.

At the Etihad, an early Rodrygo goal looked set to earn Real victory only for De Bruyne to make it all square 14 minutes from time with City having laid siege to Andriy Lunin’s goal. But after the scores remained the same after extra-time, missed penalties from Silva and Mateo Kovacic would see City’s reign as European champions ended after a 4-3 shoot-out loss, with Antonio Rudiger slotting home the winner.

Real manager Ancelotti said: “We defended really, really well tonight. This was about survival. Madrid is a club based on always fighting to stay in situations where there seems to be no way out – but we always find a way. By the time the penalty shoot-out came, we were totally convinced we’d go through.”

The Spaniards would go on to beat Bayern Munich 4-3 over two legs in the last four before beating another German side, Borussia Dortmund, 2-0 in the final, thanks to goals from Dani Carvajal and Vinicius. That made it 15 European crowns for Real.

2024/25

Knockout phase play-off – Real win 6-3 on aggregate

A comfortable victory in the end for holders Real in the revamped tournament. Haaland had twice put City in front in the first leg in Manchester only for Kylian Mbappe and then Braham Diaz to level the scores again. Jude Bellingham’s injury-time finish would give Real the advantage heading back to the Spanish capital.

At the Bernabeu, first-half goals from Mbappe would kill off the contest with the French forward completing his hat-trick just after the hour mark. Nico Gonzalez’s stoppage-time goal provided scant consolation for a disappointing City.

Real manager Ancelotti said: “This has been the complete performance – attack, defence, with the ball and without the ball, we showed such high levels of quality. We created so many goal chances. Almost the perfect night.”

Any hopes of European crown No 16 for Real were crushed by Arsenal in the quarter-finals with the English side running out 5-1 victors on aggregate.