- 2016-17: Eliminated by Monaco on away goals in last 16, won first leg at home 5-3, lost second leg away 3-1.
- 2017-18: Eliminated by Liverpool 5-1 on aggregate in quarter-finals, lost first leg away 3-0, lost second leg at home 2-1.
- 2018-19: Eliminated by Tottenham on away goals in quarter-finals, lost first leg away 1-0, won second leg at home 4-3.
Pep Guardiola suffered another dose of Champions League misery with Manchester City on Wednesday as his side were knocked out by Tottenham on away goals after a sensational quarter-final second leg at the Etihad Stadium.
Guardiola has failed to reach the Champions League semi-finals in any of his three seasons as City manager, extending his long wait to win the tournament for the third time - with his last triumph coming as Barcelona boss in 2011.
Here AFP Sport looks at Guardiola's frustrating exits from Europe's elite club competition:
2016-17: Eliminated by Monaco on away goals in last 16, won first leg at home 5-3, lost second leg away 3-1.
Guardiola's first Champions League campaign with City came to a surprising end against French side Monaco, featuring a young Kylian Mbappe.
Monaco scored three times at the Etihad Stadium in the first leg, but City hit four in the second half to seemingly take control of the tie.
However, in the second leg hapless City couldn't prevent Tiemoue Bakayoko's late goal handing Guardiola his first Champions League last 16 exit as a manager.
2017-18: Eliminated by Liverpool 5-1 on aggregate in quarter-finals, lost first leg away 3-0, lost second leg at home 2-1.
Traumatised by the vicious reception from a huge mob of Liverpool fans who attacked the City team bus with missiles outside Anfield, Guardiola's team crumbled in the first leg.
Goals from Mohamed Salah, Alex Oxlade-Chamberlain and Sadio Mane put Liverpool three up by the 31st minute.
In the return in Manchester, City scored early on through Gabriel Jesus, but never built up enough momentum for a comeback as Salah and Roberto Firmino struck for the Reds after half-time.
2018-19: Eliminated by Tottenham on away goals in quarter-finals, lost first leg away 1-0, won second leg at home 4-3.
Handed a golden opportunity to take the lead in the first leg at the Tottenham Hotspur Stadium when Danny Rose's handball conceded a first half penalty, City blew it as Sergio Aguero's spot-kick was saved by Hugo Lloris.
Even an injury to Tottenham striker Harry Kane couldn't inspire Guardiola's side, who played a cautious game and were beaten by Son Heung-min's late goal.
Roaring into a 4-2 lead after trailing 2-1 in the second leg, City were heading for the semi-finals until disaster struck in the 73rd minute when Fernando Llorente bundled home despite a VAR review of a potential handball by the Tottenham striker.
In an incredible finish, Guardiola was punching the air in delight when Raheem Sterling fired what looked to be a last-gasp winner, only for VAR to rule it out for offside.