Manchester City’s quest to win the Champions League is over for another year, having been beaten by Real Madrid in remarkable circumstances in the semi-finals.

Pep Guardiola’s side looked set to reach a second consecutive final, having taken a 5-3 lead on aggregate.

But Madrid forced extra time thanks to two extremely late goals from Rodrygo, before a Karim Benzema penalty proved decisive.

Despite so much glory in England – including a 100-point Premier League campaign and a domestic treble – City are still missing the final piece of the major trophy puzzle.

Here’s a season-by-season look at City’s history in Europe’s elite club competition.

MORE: Guardiola struggles in Real Madrid’s biggest comeback

1968/69

Eliminated step: First round

City’s first involvement came when the competition was known as the European Cup, when only the defending champions from each major nation qualified. They were knocked out by Turkish giants Fenerbahce in the first round.

2011/12

Eliminated step: Group stage

Three years after their takeover, City entered the Champions League. However, they were in a tough group containing Napoli, Bayern Munich and Villarreal, quite understandably failing to progress. Roberto Mancini’s men fell in the Europa League, where they went out in the round of 16.

2012/13

Eliminated step: Group stage

There was another tough group for City the following season, as they faced Real Madrid, Borussia Dortmund and Ajax. They finished bottom with just three points, as the battle for coefficient points was clearly hurting the new powerhouse with those daunting draws.

2013/14

Eliminated step: Round of 16

On this occasion, City went through the group stage, finishing 2nd behind defending champions Bayern Munich. However, City were knocked out by Barcelona in the round of 16, with Lionel Messi and Dani Alves both scoring in both legs.

2014/15

Eliminated step: Round of 16

City again finished 2nd behind Bayern in the group stage, this time after beating the German giants with a hat-trick from Sergio Aguero. And once again they lost to Barcelona in the first knockout round, with the Spanish side winning 3-1 on aggregate – this time powered by ex-Liverpool striker Luis Suarez on their way to claiming the treble .

2015/16

Eliminated step: Semi final

It was the first season in which City made major progress in the Champions League. After coming out of a group including Juventus, Borussia Mönchengladbach and Sevilla, they beat Dynamo Kyiv and PSG. Eventually, Manuel Pellegrini faced former club Real Madrid, losing 1-0 on aggregate to end his tenure at City.

2016/17

Eliminated step: Round of 16

Now led by Pep Guardiola, City had to go through the play-offs by beating Steaua Bucharest. The English side then finished 2nd behind Barcelona in Group C. In a hugely entertaining round of 16, they ended up drawing 6-6 on aggregate against Monaco, with the Ligue 1 underdogs winning on the rule of away goals.

2017/18

Eliminated step: Quarter-finals

City emerged from a group that included Shakhtar Donetsk, Napoli and Feyenoord. They then beat Basel in the round of 16, but were beaten by Liverpool in an all-England quarter-final clash. It was a match that marked the start of a modern rivalry with Jurgen Klopp’s men, as Mohamed Salah became the hero in an iconic 5-1 aggregate win for the Reds.

2018/19

Eliminated step: Quarter-finals

Once again, City have lost to their Premier League opponents in the last eight games, with Tottenham Hotspur taking the upper hand this time. City were in a group with Lyon, Hoffenheim and Shakhtar Donetsk before defeating Schalke in the round of 16. In the quarter-finals, the away goals rule once again proved to be decisive as Fernando Llorente claimed the winner in a game that is best remembered for VAR. knocking down a “winner” of the late Raheem Sterling.

2019/20

Eliminated step: Quarter-finals

City were knocked out in the quarter-finals, in what was quickly becoming a trend. Shakhtar Donetsk, Dinamo Zagreb and Atalanta were in their group and Guardiola’s side then got the better of mighty Real Madrid in the round of 16. However, City lost to Lyon in the quarter-finals, with a draw played in Lisbon. due to the Covid pandemic.

2020/21

Eliminated step: Final

Last season City reached the Champions League final for the first time in their history. They topped Group C, which also included Porto, Olympiacos and Marseille, before overtaking Borussia Dortmund and PSG in an impressive knockout stage. Chelsea, however, beat City in the final, with Kai Havertz picking up the winner in Portugal.

2021/22

Eliminated step: Semi-finals

This season, City topped their group, finishing ahead of PSG, RB Leipzig and Club Brugge. City then overtook Sporting and Atletico Madrid, looking to stage an all-English final with fierce enemies Liverpool. Real Madrid had other ideas though, pulling off a sensational late comeback 5-3 on aggregate.