Manchester City's exit on away goals is the first time the former Barcelona and Bayern Munich boss has departed the competition at the last-16 stage
Manchester City's exit in their last-16 Champions League clash at the hands of Monaco is the earliest stage Pep Guardiola has been eliminated from the tournament in his coaching career.
Guardiola most successful after 100 European games.
The Premier League visitors bowed on away goals in a 6-6 aggregate scoreline that featured a wild 5-3 first-leg win for them at the Etihad Stadium.
It was a result that established them as favourites for their trip to France, with Sergio Aguero or Leroy Sane - so potent in recent games - were expected to be able to secure a crucial away goal.
However, Monaco - despite missing the services of the injured Radamel Falcao - roared back to claim a 3-1 result at Stade Louis II, courtesy of two goals scored by Kylian Mbappe and Fabinho in the first half.
Leroy Sane put City back in front after the break, but Tiemoue Bakayoko scored the clincher shortly after that to send former Barcelona and Bayern Munich boss Guardiola out of the Champions League in the last-16 for the first time.
After failing to muster a single shot in the first half, City also made history by becoming the first side to ever exit the Champions League in a knockout tie after scoring five goals in the first-leg.