In the end they failed with their deadline day bid for the player after several goalposts were moved in the deal - and Daniel Levy subsequently pulled the plug.
This summer they were expected to rekindle their interest, but Andre Villas-Boas had moved on - and so had Moutinho.
The Portuguese international celebrated his own excellent season with Porto by leaving the club for mega bucks - with AS Monaco his destination.
The free spending principality have thrown around the cash this summer, bringing in top players such as Radamel Falcao, James Rodriguez, Eric Abidal, Geoffrey Kondogbia and Ricardo Carvalho.
All the deals were shocks considering the fact Monaco only recently earned promotion to the top flight of French football - but being bankrolled by a Russian billionaire always has it perks, doesn’t it Chelsea fans.
But you might think that a player such as Moutinho might regret never playing for a bigger club than Sporting Lisbon, Porto or Monaco.
As respectful as you can be to all three outfits - there is little doubt that Moutinho is a player who had the talent to grace both the Premier League and La Liga - while the Bundesliga and Serie A could also have afforded him the chance to play for some massive teams.
But despite this, Moutinho has been speaking of his career in the last couple of days - and refuting the idea that he should consider Monaco any less of a club than the likes of Real Madrid, Barcelona or Manchester United:
"I think I played in big clubs. The Sporting and especially Porto where I lived extraordinary things.But are we talking about here? Of why Manchester, Barcelona or Real never came looking for me? It does not matter. I'm in a big club now and the club has the ambition to compete with these teams there. "
It was rumoured that United could have made a move for the player this summer, as David Moyes tried to snap him up on multiple occasions as Everton boss.
But for Moutinho he appears to be as happy at Monaco as he has anywhere in his career - and we don’t blame him with the favourable tax rates.
As for Monaco, well they aren’t doing badly either. Top of Ligue 1 after five games and still unbeaten - who knows, they could end up winning the title ahead of the 2015 schedule put in place.
Is Moutinho right? Are Monaco rivals for Barca and United?
image: © goulao