In 2009, Guardiola had his first taste of European success with a formidable Barcelona side, one which will be forever etched in the history books.
Two years later and the Spanish coach had made it two Champions League titles in quick succession. However, seven years have since passed and the 47-year-old is still waiting for his third appearance on that famous podium.
He couldn't do it again with Barcelona, or with Bayern Munich - a fact which led to his downfall at the Bavarian club - and now faces an uphill battle to achieve the feat in his second season in charge of City.
Guardiola has come close on several occasions, losing out in the semi-finals in his three years in charge of Bayern, but if he is to reach that stage of the competition, his side must overturn a three-goal deficit to Liverpool in the return fixture on Tuesday.
Having failed to score at Anfield, City cannot afford to let their opponents score first as it means they would need five goals to turn their tie in their favour. Although, they do boast one of the most prolific attacks in Europe and will need to go all guns blazing at the Etihad.
Thoughts of a treble still persist in Manchester and they will not give up on their Champions League dream without a fight. It will be a tough ask, but they have dominated numerous teams already this season and will need a near-perfect game to reach the semi-finals.