Sergio Aguero didn't get the farewell he wanted while Kevin De Bruyne suffered a heartbreaking early end as Manchester City were stunned by Chelsea in the Champions League final.
The two City legends were both reduced to tears on a night that just wasn't theirs, with Kai Havertz's first-half goal leading Chelsea to European glory.
For De Bruyne, he was forced out of the game on the hour mark after suffering a nasty head injury.
De Bruyne clashed with Chelsea defender Antonio Rudiger, which left the Belgium playmaker with a black eye and needing treatment for a number of minutes.
The 29-year-old could not continue and was visibly upset leaving the pitch.
Tears flowed down his face and he was comforted by City staff on the touchline, including boss Pep Guardiola.
His early withdrawal was a huge blow for the Premier League champions and they failed to find a way back into the match without their talisman.
De Bruyne gave an update on Sunday morning to his condition.
He wrote on Twitter: "Hi guys just got back from the hospital. My diagnosis is Acute nose bone fracture and left orbital fracture. I feel okay now. Still disappointed about yesterday obviously but we will be back."
Meanwhile, there was devastation on the part of Aguero too as City's all-time top scorer said goodbye to the club.
Aguero, 32, had promised to win the Champions League before he left but was unable to do so.
He appeared as a late substitute on his 390th and final appearance for the club and hardly had a kick.
He was pictured in tears on the pitch at the end of the game, as he prepares to join Barcelona on a free transfer.
Aguero can hold his head high as he departs though having cemented his status as a City icon.
His career at the club yielded 260 goals and 12 major trophies, including five Premier League titles.