As City grew in power and prestige through their mega buck investment over a decade ago, there were high expectations for a side which featured a lineup worthy of winning absolutely everything. Yet it's been painstakingly difficult for City to assert themselves on Europe's highest platform.
The current one-legged formatting of the Champions League - due to the coronavirus pandemic - suits Pep's side down to the ground. After all, two-legged European ties have proven to be rather complicated for the Cityzens.
The cruel but fair nature of City's quarter final exit to Tottenham last season was a difficult VAR pill to swallow. The spectacular exit at the hands of Monaco some two years ago, a tie in which City blew a 5-3 lead from the first leg, wasn't particularly enjoyable for the club's fans either.
Pep's side showed vast improvement to come away from the round of 16 with a 4-2 aggregate win over recently crowned La Liga champions Real Madrid. It was no easy task by any stretch of the imagination, yet City executed a cunning performance in the second leg.
Pep's side forced Madrid into mistakes and showed a clinical eye in front of goal, displaying the exact characteristics needed to win the tournament.
You get the impression that the intensity of this new winner-takes-all format is something Pep is relishing. He is perhaps the most intense manager in world football, and arguably the most talented, yet it has been nine long years since he won his last Champions League with Barcelona in 2010/11.
Having won everything else domestically with both Bayern Munich and City, Pep will be champing at the bit to get his hands on Europe's most coveted trophy once again.
The Sky Blues blew their chance at three Premier League titles in a row as Liverpool clinched top spot for the first time in 30 years, but it's the Champions League Pep will be demanding of his star-studded.
He did famously claim ahead of their Group C match with Atalanta that City were not ready to win the tournament due to a lack of clinical ability. You'd be surprised if his stance hasn't changed since then.
After their shock dispatching of Serie A champions Juventus, Lyon await the Cityzens in the quarter finals on Saturday. It is a chance for revenge following a 2-1 home loss in last season's competition in Group F, but it is ultimately a match that you would expect City to come away from with the win.
Pep's side are unbeaten in the Champions League this season, and despite their failure to match Liverpool domestically, you could argue that this is one of the strongest City sides we have seen so far. It is certainly the best we have seen from both Kevin De Bruyne and Raheem Sterling, with the duo in mesmerising form and proven difference makers for the team.
De Bruyne's ability to boss the midfield and dictate the tempo of the game are traits that flatter Pep's tactical style, while Sterling's final ball and finishing ability have come on leaps and bounds. Fernandinho's ball-playing skills have been invaluable in his transition to central defence, while Gabriel Jesus is enjoying his most prolific spell for the club in the absence of Sergio Aguero.
City scored a mammoth 102 goals in last season's Premier League, and in these one-legged shootout affairs, it is a record that should serve the Sky Blues well as they aim to clinch their first ever Champions League trophy.
The defensive record is there too. Ederson will carry confidence into the latter stages of the tournament following his Golden Glove winning campaign, as the Cityzens conceded just 35 goals.
It's looking promising for City. The quality in the squad is there in every area of the pitch. Providing they can cope with the pressure, this can certainly be their year.