Silva is set for a Sunday reunion with the London club in an FA Cup quarter-final, and he certainly does not regret turning them down as a teenager.
He was scouted as a 15-year-old by the Stamford Bridge side in 2005, with Jose Mourinho even taking time to speak to him and two young team-mates.
However, his club took a hard-line approach on the manner the Premier League champions conducted their business, issuing a complaint to FIFA and denying the young midfielder the opportunity to train with them for two months.
Fabio Ferreira and Ricardo Fernandes ultimately moved to England only to be released after four years in which they failed to play, but Silva chose a different route.
“Thanks to God,” he told the Guardian, citing worries that Mourinho’s side “wanted to win now and not wait for young players”.
“It was a very strange moment and I was so young,” he remembered. “To have this club approach me, especially when Mourinho comes to talk to you … at this time, we didn’t know why he came. But when the club wants something, they do everything.
“He came to see me in Portugal and we went there, to Chelsea, to see the training ground. Then we came back and it was a big, big situation with Sporting.”
Over a decade later, he finally moved to England, although he endured more frustration as he was not allowed to play for the Foxes until January as they registered his summer move 14 seconds past the deadline.
“I had some injuries in my career but then you know why you don’t play and that’s part of football, so you can accept it,” he complained. “But this situation wasn’t correct. It wasn’t correct because I was able to play physically and I didn’t do anything wrong to make this situation.
“I will never understand the decision of Fifa – even after Leicester had tried everything to change it.
“OK, if it is so many hours [after the deadline], but we’re talking about seconds here. So I think it was a very poor decision.”
He has made eight appearances for his new side, creating two goals.