Guardiola moved to the Premier League from Bayern Munich in 2016 and needed a number nine whom he trusted as he rebuilt the club in his image.
Nolito was 29 when he arrived - around the same time as Ilkay Gundogan - on the back of three successful years with Celta Vigo, but unfortunately couldn't replicate his influence at the Etihad Stadium.
The Spaniard scored just six times in 30 appearances for City before leaving for Sevilla, then back to Celta and has now retired from playing at 36 years old after a stint in the third division with Ibiza.
But the experience of playing with the toughest around has stuck with him having played for two European giants in City and Barcelona.
Nolito joined Barcelona at the age of 22 where he made five senior appearances alongside more than 100 for the club's famous B team.
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During his time at the Nou Camp he was able to play alongside Xavi, Andres Iniesta and of course, football's GOAT Lionel Messi who was really entering his prime in the 2010/11 campaign.
Nolito also got to play alongside generational talents such as Kevin De Bruyne and Sergio Aguero, while also coming up against some of the Premier League's toughest stars in Vincent Kompany, Yaya Toure and Fernandinho.
He even had the chance to play alongside Carles Puyol, Gerard Pique and Eric Abidal, along with Sergio Busquets and Javier Mascherano during his formative years in Catalonia.
However, the toughest player he ever faced wasn't a Premier League player or a teammate from Barcelona or Man City, but instead a La Liga veteran who played for Elche and Getafe.
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Speaking on the El Partidazo de Cope podcast, he said: "It was Damian [Suarez], the one from Getafe, especially without the ball.
"I used to tell him 'pisha' give me time when I have the ball, you're going to put your tibia in my ear. But he was a nice dude. At the end [of the day] it's a contact sport."
Apart from his year in Manchester and a short stay at Benfica, he spent his career in his native Spain where the weather was considerably better.
Speaking in 2017, when angling for a transfer out of the country, he said: "I have learnt very, very little English - it's very hard. Just 'tomorrow', 'good morning', 'good afternoon' and a little more.
"My daughter's face has changed colour - it looks like she's been living in a cave."
But while his playing days may be done, the forward will undoubtedly have some pretty special memories after rubbing shoulders with the best in football.