Manchester City's relationship with the Champions League isn't exclusively a contemporary one.
The club's maiden appearance in the competition came way back when during the 1968/69 season, but their disappointing early exit would foreshadow future continental woes.
City have evolved into a juggernaut under Pep Guardiola; a side so often regarded as the very best Europe has to offer. A team as coherent and talented as the Sky Blues are worthy of multiple Champions League crowns, exemplified by their domination of a hugely competitive Premier League, but Guardiola's Citizens have perpetually come up short on the European stage.
While Pep's stint in Manchester has been nothing short of scintillating, the Spaniard's not yet been able to fit the final piece into his jigsaw.
How many times have Manchester City won the Champions League?
Manchester City have featured in the Champions League 12 times, and in every season since 2011/12, but they've never yet won the competition.
Their maiden European Cup entry after being crowned First Division champions in 1968 culminated in a round of 32 exit at the hands of Fenerbahce. The club drifted in and out of obscurity thereafter, jumping between divisions, before stability was established throughout the noughties which climaxed in an ownership change that brought about relevancy to the sky blue side of Manchester.
United's noisy neighbours were as loud as ever as they dramatically claimed their first Premier League title at the end of the 2011/12 season - a first since 1968. City's rise saw them emerge as regulars in UEFA's premier club competition, but they simply weren't on the level of Europe's behemoths during the formative stage of their journey.
City began the decade with back-to-back group stage exits before Barcelona schooled them twice in the round of 16 in both 2014 and 2015. Qualification into the knockout stages signalled progression, however, and they continued on their linear trajectory in 2015/16 as they reached the semi-finals for the first time under Manuel Pellegrini. Real Madrid, though, squeaked out a 1-0 victory over two legs before going on to win the competition.
Despite their domestic success, City's expectations in Europe were relatively low before the arrival of Guardiola in 2016. The two-time Champions League winner had failed to claim glory in the competition at Bayern Munich, but his status as the finest manager of his generation from two previous continental triumphs with Barcelona stood the Citizens in good stead.
However, Guardiola's quest to bring the trophy to Manchester has thus far been compromised by misfortune, his own genius, and bloody Real Madrid.
A swashbuckling Monaco edged them out on away goals in the last 16 during Pep's first season, before City suffered three consecutive quarter-final exits at the hands of inferior opposition. His side succumbed to the Anfield cauldron in 2018, the introduction of VAR against Tottenham in 2019, and, well, a surprise package Lyon during the Covid-hit campaign of 2019/20.
Lyon's 3-1 victory was surely the most humiliating of City's Champions League exits to date.
2020/21 finally saw City fulfil their potential on the European stage as they beat Borussia Dortmund and a superstar-laden Paris Saint-Germain to advance to their first-ever Champions League final. However, Thomas Tuchel, who had overseen two victories against City during the second half of the domestic season, masterminded yet another triumph over the Guardiola in Porto as the unfancied Chelsea were crowned European champions instead.
Guardiola was chastised for his team selection, as his side fell flat against familiar opposition.
Nevertheless, City were once again in fine form a season later, and they looked for all money to progress into another all-English final when they took a 1-0 lead over Real Madrid in the second leg of their semi-final tie. City's aggregate advantage was 5-3 entering the closing stages before Los Blancos restored parity before the full-time whistle. City's exit then became inevitable, and it was Karim Benzema who thrust the dagger into sky blue hearts as he converted a penalty in extra-time.
The unimaginable nature of City's defeat in the Spanish capital raised questions of whether it'll ever happen for Guardiola in Manchester, but the arrival of Erling Haaland has reignited hope that the Champions League will finally enter the club's trophy cabinet.
Every Manchester City Champions League appearance
This article was originally published on 90min as How many times have Manchester City won the Champions League?.