You might even choose his 2014 move to Chelsea, which, despite a Premier League title, only lasted a single-season before heading back to Atletico Madrid.
However, for the now-retired Brazilian, one moment stands out above the rest.
Speaking on the Charla Podcast days after his retirement from football at Flamengo, the 38-year-old recalled when he got dragged down to the trenches in his first Madrid derby in 2010.
"I'm going to open my heart about the biggest regret of my career," he said.
"If there is something that I really regret having done, and I would like to go back in time and not do it again, it was to Angel Di Maria.
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"I arrived at Atletico Madrid and we were going to play against Real Madrid. Kun Aguero told me 'Filipe, if you get close to him, he will get lost, he will leave the game. At the first opportunity, talk to him about his wife'.
"When I got to Di Maria, I told him: 'Your wife…' I don't know what [I said]. I cursed him, I said his wife's name.
"Then he looked at me, he was crestfallen, I dominated him the whole game. And he really didn't have a good performance.
"I got home and I regretted it so much. To Di Maria, a thousand apologies, friend, sorry for having done that to you."
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Di Maria's wife, Jorgelina Cardoso, may jog the memories of some, as she previously made headlines with her views of England.
The Argentine World Cup winner joined Manchester United in 2014 for an ill-fated £60million stint, and his wife later commented that: "The people are all weird. You walk around and you don't know if they're going to kill you.
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"The food is disgusting. The women look like porcelain."
However, she did also comment that part of their justification for the move was due to their friendship with Aguero and his wife, something which Felipe Luis may have now put in danger…