- 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.