A look back at Manchester City's previous five Champions League exits
Manchester City's defeat to Monaco on Wednesday means they have failed to reach the Champions League quarterfinals for the fifth time in six years. The club's poor performance in Europe will look even worse on Friday morning when Leicester City go into the last-eight draw at their very first attempt.
There have been memorable nights in the competition -- victories over European super-powerhouses such as Barcelona, Bayern Munich and Paris Saint-Germain -- but generally it is a competition in which City's stellar squad has underperformed.
One of the reasons for Pep Guardiola's arrival was to change the club's fortunes in Europe despite some claiming he failed during his three years at Bayern because he didn't win the Champions League there. But his first European season at the Etihad as ended prematurely with Guardiola failing to reach the semifinals for the first time in his coaching career.
Here's how City's other seasons in the Champions League have gone:
After narrowly missing out on Champions League football the previous season, City finished third in the Premier League to qualify for Europe's top competition for the first time in 32 years.
But they were handed a tough draw and were immediately under pressure to qualify for the knockout stages after drawing at home to Napoli and losing at Bayern. Back-to-back victories over Villarreal gave Roberto Mancini's side hope of reaching the last 16 but they needed a miracle after a 2-1 defeat to Napoli in Italy.
A 2-0 victory over Bayern on the final matchday wasn't enough as Napoli won in Spain and City were eliminated with 10 points, which would have been enough to progress from six of the eight groups that season.
A seeding system, based on previous European performance, resulted in City being drawn into a tough group comprising the champions of England, the champions of Spain, Real Madrid, the champions of Germany, Borussia Dortmund, and the champions of the Netherlands, Ajax.
Mancini's team looked to have made a perfect start when Aleksandar Kolarov put City 2-1 ahead in the 85th minute of the opener in the Santiago Bernabeu. But two late goals from Karim Benzema and Cristiano Ronaldo saw Real snatch a 3-2 win.
City didn't recover from the setback and failed to win a single group game as they exited bottom of Group D with just three points and the poor performance contributed to Mancini's departure before the end of the season.
Manuel Pellegrini arrived in the summer with a reputation for success in Europe after overachieving at Villarreal by taking them to the semifinals and then leading unfancied Malaga to the last eight.
He did at least take City out of the group stage for the first time, but his reputation took a battering in the final group game when his misjudgement cost them the possibility of finishing top of the group.
City had fought back from 2-0 down in Bayern to lead 3-2 in the Allianz Arena and another goal would have seen them top the group. But Pellegrini didn't push forward for another despite qualification being assured.
It meant they were drawn against Spanish champions Barcelona and City were thoroughly outclassed, losing 4-1 on aggregate.
City looked to be heading out of the group stage after failing to win any of the opening four group games.
They trailed Bayern 2-1 at home in the fifth before Sergio Aguero turned the game around with two brilliant strikes to secure a hat trick and 3-2 win. It meant City needed to win their final game against Roma and, despite being without Aguero, Yaya Toure and Vincent Kompany, they produced one of their best European performances to win 2-0 in the Stadio Olimpico.
But they were paired with Barca again in the round of 16 and despite losing by a slightly better 3-1 scoreline on aggregate, they were grateful for Joe Hart's heroics in the Camp Nou to keep the score down. The England keeper produced an outstanding performance, which even Lionel Messi commented on, saying: "He was phenomenal, he stopped everything."
Pellegrini's departure was announced in February, but he went on to produce City's best-ever performance in Europe in what fans hoped would be a breakthrough season. City topped a group for the first time -- ahead of Juventus, Sevilla and Borussia Monchengladbach -- and then eased past a poor Dynamo Kiev in the last 16.
They overcame PSG in the quarterfinals 3-2 on aggregate to set up a semifinal return to Real.
But City were far too defensive and barely threatened the Spanish side over the two legs. After a 0-0 stalemate at the Etihad, they fell behind to a Fernando own goal in Madrid and couldn't produce the one opportunity that could have seen them sneak into the final on away goals.
Jonathan is ESPN FC's Manchester City correspondent. Follow him on Twitter: @jonnysmiffy.