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.
1 – This is the first time that a side managed by Pep Guardiola has exited the Champions League at the Last 16 stage. Blushes.— OptaJoe (@OptaJoe) March 15, 2017
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.
5 – Man City are the first team in Champions League history to be eliminated in a knockout tie after scoring 5 goals in the first leg. Wild.— OptaJoe (@OptaJoe) March 15, 2017
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.