Manchester City's elimination from this season's Champions League is undoubtedly Pep Guardiola's darkest day as manager of the club.
The Citizens were tipped by many as the favourites to win the competition, but Lyon defied the odds last night in Lisbon to claim a memorable 3-1 victory.
It's the latest edition in a series of European failures for Guardiola at City and this one is made worse by the fact that Lyon finished seventh in Ligue 1 this season.
But City's loss to the French side is far from the team's only poor showing under Guardiola's leadership.
Below, we've provided nine more of the club's humiliating defeats since the Spaniard took charge back in the summer of 2016.
Leicester 4-2 Man City, 2016/17
After winning the title in 2015/16, Leicester endured a tumultuous campaign the following year which saw them flirt with relegation.
Teams were turning them over left, right and centre - everyone bar City.
A hat-trick from a hopelessly out of form Jamie Vardy handed Guardiola his first taste of humiliation in English football.
Everton 4-0 Man City, 2016/17
It's hard to think of a worse performance from a Guardiola team than this one.
City were comprehensively outplayed by Everton at Goodison Park from the first whistle until the last.
Tom Davies' solo effort was the pick of the goals on the day and it's still the only time City have lost by a four-goal margin in the Premier League under Guardiola.
AS Monaco 3-1 Man City, 2016/17
City won the first first-leg of their Champions League tie against Monaco 5-3 and were expected to seal progression to the quarter-finals.
Goals from Kylian Mbappe and Fabinho then put the French side in the driving seat, before Leroy Sane scored a priceless away goal.
But a late header from Tiemoue Bakayoko made sure that Guardiola's first European campaign with City ended in disaster and it's a trend that's continued ever since.
Man City 1-2 Liverpool, 2017/18
A classic all-English Champions League quarter-final.
After being destroyed 3-0 at Anfield in the first leg, Guardiola's side were eager for revenge and took an early lead through Gabriel Jesus at the Etihad.
But second half strikes from Mohamed Salah and Roberto Firmino secured a convincing 5-1 aggregate win for the Reds, condemning the City boss to yet more misery in European competition.
Wigan 1-0 Man City, 2017/18
'1-0, Will Grigg, up the 'Tics!'
One young fan's famous prediction before Wigan's meeting with City in the FA Cup famously came to fruition back in 2018.
City had 82% possession against the League One side, but it counted for absolutely nothing.
Norwich 3-2 Man City, 2019/20
City's 2019/20 campaign got off to a dreadful start as they were outplayed by newly-promoted Norwich.
Teemu Pukki and Emi Buendia tore Guardiola's defence apart, handing Liverpool the early initiative in the title race.
City's haplessness in defence against the Canaries was a sign of things to come.
Man City 0-2 Wolves, 2019/20
The day Adama Traore made the Etihad Stadium his own personal playground.
City looked bereft of ideas against Wolves' stubborn defence and were made to pay by Traore on the counter.
The Spaniard scored twice in the final 10 minutes as City managed just two shots on target all game.
Wolves 3-2 Man City, 2019/20
Wolves really did a number on City in 2019/20.
Ederson was sent off early in the game at the Molineux Stadium, but two goals from Raheem Sterling had the victors 2-0 up with 50 minutes played.
What followed was an implosion of epic proportions. Goals from Traore, Raul Jimenez and Matt Doherty secured all three points for Wolves and effectively ended City's faint hopes of Premier League glory.
Arsenal 2-0 Man City, 2019/20
City were supposed to stroll past Arsenal to reach this year's FA Cup final.
Mikel Arteta had other ideas, though. Guardiola was unable to breach the Gunners' stubborn defence as his former protege outwitted him at Wembley.
David Luiz decided to turn into Virgil van Dijk for 90 minutes, while Pierre-Emerick Aubameyang was as clinical as ever at the other end of the pitch.
City are a great team, of that there is no doubt. But there's also no denying that they're prone to an embarrassing defeat and the less said about their exploits in Europe, the better...