Both managed to keep in tact the Premier League's unbeaten start to life in the competition after three rounds of matches, but one manager certainly went home the happier.
Jose Mourinho's United side managed to grind out a 1-0 win away in Benfica, courtesy of a fluke Marcus Rashford free-kick, pretty much sealing their passage to the knockout stages.
However, the 'Special One's' bitter rival Antonio Conte certainly will have not returned home in a buoyant mood, as his depleted Chelsea side was held to a 3-3 draw by Roma at Stamford Bridge.
The Blues were 2-0 up, but simply couldn't handle former Manchester City man Edin Dzeko, with the Bosnian striker scoring a brilliant brace.
It leaves Chelsea's group in a precarious place, particularly as Atletico Madrid could only manage a 0-0 draw with Qarabag in Azerbaijan.
Conte is under a lot of pressure right now, particularly with the injuries in his squad.
In typical Mourinho fashion, the United boss decided to try and rile his nemesis by stating that managers shouldn't 'moan and cry' about losing players throughout the season.
"And there is another situation, maybe I'm guilty of it: I never speak about injuries," said Mourinho.
"Other managers, they cry, they cry, they cry when some player is injured. I don't cry.
"I think the way to do it is to ignore the players that are injured, is to focus on the players that are available. It is to give confidence to the players that are available."
Sounds a bit ironic, right?
Everyone knows Mourinho loves a little whinge, particularly if anything happens to not go his way.
Conte was then told by the press in his press conference what Mourinho had said and the Italian reacted brilliantly.
"A lot of time Mourinho has to see what happens at Chelsea," he said.
"A lot of time, also last season. I think he has to think about his team and stop... to look at himself, not the others."
To be fair, at no point in Mourinho's interview did he mention Chelsea, so were the media dangling some bait and Conte simply bit?
Knowing Mourinho, he probably was referring to his former club.
The two managers meet for the first time on November 5 at Stamford Bridge and the United boss will be keen to banish the memories of the 4-0 thrashing handed out to him in the same fixture last season.