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Guardiola failed to reach the Champions League Semi-Finals in none of his three seasons as a city manager, extend his long wait to win the tournament for the third time – with his latest triumph to come as Barcelona boss in 2011.
AFP Sport examines Guardiola's frustrations with the European club competition:
2016-17: Eliminated by Monaco on goals scored away in the last 16 games, they won the first leg at home 5-3, lost the away match to the outside 3 -1.
Guardiola's first campaign with City, in the Champions League, ended surprisingly against the French team of Monaco, with the young Kylian Mbappe.
Monaco scored three times in the first leg against Etihad Stadium, but City scored four in the second half to seemingly take control of the game.
However, in the return leg, the unlucky city could not prevent Tiemoue Bakayoko's goal of giving Guardiola his first appearance as a manager for the Champions League.
2017-18: Eliminated by Liverpool 5-1 overall in the quarterfinals, defeats in the first leg 3-0, lost in the first leg 2-1.
Traumatized by the vicious reception of a crowd of Liverpool supporters who attacked the city team bus with missiles in front of Anfield, Guardiola's team is collapsed in the first leg.
Goals from Mohamed Salah, Alex Oxlade-Chamberlain and Sadio Mane gave Liverpool three goals in the 31st minute.
Back in Manchester, City scored early thanks to Gabriel Jesus, but he never had enough momentum for a comeback while Salah and Roberto Firmino hit the Reds after halftime.
2018-19: Eliminated by Tottenham thanks to goals in the quarter-finals, a 1-0 loss to the away game, a 4-3 home victory.
A golden opportunity to take advantage in the first leg at Tottenham Hotspur Stadium when Danny Rose's ball conceded a penalty kick in the first half. City missed an opportunity as Sergio Aguero's free-kick was saved by Hugo Lloris.
Even an injury to Tottenham striker, Harry Kane, could not inspire the Guardiola team, who played a cautious game and was beaten by Son Heung-min's goal .
Rising to 4-2 after being 2-1 in the second leg, City headed to the semi-finals until disaster in the 73rd minute when Fernando Llorente won the match against his teammate, despite the fact that VAR had examined the potential of the Tottenham striker.
In an incredible finish, Guardiola was delighted when Raheem Sterling dismissed what appeared to be a last-minute winner, but VAR had to exclude him from the offside.
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