Go back eight years and the modern-day Manchester City’s first European game as champions of England came in the Bernabeu. They led 1-0 and 2-1 but lost to a last-minute goal by one of the two defining players of the Champions League this century, in Cristiano Ronaldo, and a club, in Real Madrid, who now have 13 European Cups. So near but yet so far, a triumph for the established order: those 90 minutes suffice as a symbolic summary of City’s Champions League fortunes. More than most, they know how narrow the margins can be. They have stories of away goals and disallowed goals, of red cards, missed penalties and mishaps, of Fernando Llorente’s hip and Lionel Messi’s twinkling feet. They have hard-luck tales, especially in Pep Guardiola’s reign. They have always come back for more. Until now, perhaps. “If we are able [to beat Real], we will be so happy,” Guardiola said on Saturday. “If we don’t, next season.” Except that, as he swiftly realised, there may be no ‘next season’ in Europe. The prospect of a Champions League ban raises the stakes. It might be now or never for their manager and for players like David Silva, Sergio Aguero and Fernandinho. At 29, Ilkay Gundogan is younger but runs the risk of seeing his ambitions thwarted. The German scored in the 2013 final for Borussia Dortmund and insisted bullishly: “I don’t believe it is going to be my only final. The Champions League is maybe the most prestigious competition and if you don't win it, as much as we are a great team, you feel like there's always something missing.” Greatness comes in different forms. Guardiola has often referenced the tradition of winning the Champions League that Real have and which he believes benefits the super-clubs. The 21st century has only provided one new winner and Chelsea were serial semi-finalists and 2008 runners-up before eventually triumphing in 2012. City have set their sights on becoming the second, but it has scarcely been a simple process. They came closest in 2016 but were perhaps too timid when they lost the semi-final 1-0 on aggregate to Real. Perhaps they had an inferiority complex then. “I am sure Man City can beat them [now],” said Pablo Zabaleta, one of that 2016 squad. Real have been the anti-City in recent years, struggling to win their domestic league but prevailing more often in Europe. Guardiola has eight league titles as a manager and Zinedine Zidane just one. The Frenchman, however, has more Champions Leagues as a manager. He has displayed a sure touch on such occasions. Guardiola boasts a winning record against Real from his Barcelona days, when his victories included a 5-0 and a 6-2, but perhaps his most demoralising defeat came to them. In the 2014 semi-finals, Guardiola went against his instincts, heeded his Bayern Munich players’ suggestions, played an unusually direct 4-2-4 and saw it backfire as they lost 4-0 at home. The Catalan subsequently described it as the worst mess-up, or words to that effect, of his career. This is his first chance to exact revenge. City’s performances against West Ham and Leicester in the last week suggest they could be galvanised by feelings of adversity. They could have Raheem Sterling fit to return against a club who have an interest in him whereas Real will be without the injured Eden Hazard, a past scourge of City. As Guardiola noted this week, the path to glory runs through the usual winners, through Real and Bayern and Barcelona. If City to be the best, they have to beat those who have been the best for decades. Because they may not have the chance to do so next season.