Chester, 27, made his debut for the club in Ronaldo’s final season at Old Trafford and will now come face to face with the Real Madrid forward after helping Wales beat Belgium to seal a last-four date with Portugal.
And having been an inexperienced teenager when he first trained with the Portuguese star, he is now relishing this prospect of locking horns with him again at the European Championship.
“I was lucky enough to train with Cristiano a few times and it was evident then what a great player he was,” Chester told Sport360. “Since he’s gone to Real Madrid his game has changed and he’s got even better – he’s turned into a goal machine. He’s obviously one we’ll have to watch.
“I was lucky as a young lad at United to see all those great players, including Ronaldo, at the top of their game. He was always very professional away from the pitch too, working in the gym and looking after himself. It was the players’ extra work off the pitch that was one of the biggest things I took from my time at United.”
The battle between Real Madrid team-mates Ronaldo and Bale will undoubtedly dominate the build-up to next week’s semi-final in Lyon and, having played with them both, Chester insists it is the Welshman who is the best player at Euro 2016.
“It’s going to be a great battle between Cristiano and Gareth, I’m sure the media will hype it up,” said Chester. “Gareth and Cristiano play together at Real Madrid but I’m glad that we’ve got Gareth on our side.
“He’s the best individual in the tournament. If we defend and play like we have done, we’ll give ourselves a great chance of beating Portugal.”
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Another ex-United presence in the Portugal ranks is Nani, a player who impressed Chester at close quarters.
“Everyone has seen the ability he has. Physically was thing that surprised me the most when he came to United. How fit, strong and quick he was. He’s got great ability.”
Asked whether Wales can now go on to win the European Championship, Chester responded with a resounding “yes”, with the West Brom centre-back proud of the progress Chris Coleman’s side have made.
“I think it’s an understatement to say we’re delighted,” Chester added. “I don’t think it’s quite sunk in, the whole journey we’ve been on since the start of the tournament. Before we came here we wanted to give a good account of ourselves and play football the way we want to play. We’re doing that at the moment and getting great results.
“We spoke after the England game, we played with a lot of fight and determination but we didn’t play with our identity. It was an important moment and now we know that the performance is the most important thing – hopefully the results will then come, just like it did tonight.”