But the Welsh prodigy was destined never to make it to football's highest level after suffering a cruel ankle injury.
Calliste has, however, found success and fortune in a world quite close to many footballers' hearts.
Players not only view high-end wristwatches as something to flaunt alongside their designer clothes, but as a shrewd investment.
Their sports cars will depreciate in value the moment they drive them out the showroom, while investments in racehorses and the stock market come fraught with risk.
Ramon Calliste was an up-and-coming star in Manchester United's academy two decades ago
Now the former player owns a £5million luxury watch business and works with footballers
Footballers value watches because they not only look good but offer a sound investment
But their Rolex, Patek Philippe and Richard Mille timepieces - some worth the equivalent of a week's wages for Premier League stars - will actually retain their value.
These young men on such eye-watering salaries also love the rarity value of exclusive watches that can't simply be bought in a shop but come invitation-only.
It's a market Calliste - who incidentally is one of just a handful of players to have bridged the divide between United and arch-rivals Liverpool - has tapped in to.
As a footballer himself, he was able to gain the trust of fellow professionals and his company, Global Watches, is believed to make £5million-a-year.
The luxury watch specialist, which has a branch in London's exclusive Mayfair, specialises in hard-to-find Rolex, Patek Philippe, Richard Mille and Audemars Piguet watches.
Some are worth in excess of £250,000. On just a normal day, Calliste says he trades watches worth between £50,000 and £70,000.
'When I realised football wasn't going to give me the life I desired, it was about setting up something else and moving fast,' Calliste, 38, told The Sun last year.
Collecting watches has become a passion for Premier League stars like Reece James and Marcus Rashford, as well as several top-flight managers
Calliste, seen playing for Manchester United's youth side as a teenager, was able to build up trust with footballers because he was an ex-pro
Marcus Rashford wears a diamond-encrusted Richard Mille RM011 at a film premiere
One of many watches in Erling Haaland's haul is a £67,995 rose gold watch made by luxury Swiss brand Vacheron Constantin (pictured)
Cristiano Ronaldo wore the £1.6million Franck Muller Invisible Baguette Diamonds Imperial Tourbillon in 2018 to a Juventus press conference
'I started to get involved in watches through contacts I had in the world of football.
'Once I saw it could become a viable business, I set up Global Watches in 2013 and it's become a really strong company that's now turning over millions.
'I dealt with footballers in the beginning, selling them watches and I already had that trust there.
'Even today, clients come online and they see it's me and they feel comfortable buying from me.
'When you can take your inventory to a room of footballers, perhaps ten millionaires, that's better for all concerned.'
It isn't just the players who appreciate a good timepiece on their wrist. A number of Premier League managers past and present also have a penchant for nice watches.
Manchester City boss Pep Guardiola has worn the Rolex Cellini, Richard Mille 010 and A Lange & Sohne Datagraph at various points.
A colourful selection of Rolex Oyster Perpetual watches from Calliste's business
A £75,000 Rolex Day-Date 128238RBR with distinctive rainbow-coloured diamond dial
Frank Lampard 'has more Pateks than the catalogue', joked James in his GQ interview, with the Swiss brand also favoured by David Moyes and Brendan Rodgers.
Mikel Arteta at Arsenal and Marco Silva of Fulham have been seen wearing Rolexes.
'Even when I was younger, 15 to 20 years ago, people were into their cars and watches,' Calliste told the Daily Telegraph.
'It's a different perspective now as they are seen as assets and investments. To see some of these players who I have contact with still and have nice pieces in their collection and paid very good money many years ago, kept them in pristine conditions and now they have gone through the roof.'
A £50k yellow gold Rolex Daytona 116508
Calliste was still at school in Cardiff when United scouts first began watching him. He was 15 when invited to Old Trafford alongside his family in 2000, meeting legendary boss Sir Alex Ferguson, who persuaded him to sign.
'I had massive respect for him and still do. He's a little bit intimidating still. Such a wise man like him has this special aura,' Calliste told the Manchester Evening News of Ferguson.
Calliste was part of the United side that won the prestigious FA Youth Cup in 2003 and was one of the players invited to train with the first team at their Carrington training base.
But in 2005, after the Football Association decided to combine club's under-17 and under-19 squads into one under-18 side, Calliste was one of the unlucky ones let go.
Ferguson broke the sad news to him on April fool's Day but it was certainly no joke.
Liverpool came in for the speedy forward but there was too much competition to make a breakthrough at Anfield.
Calliste dropped down the divisions to Scunthorpe but hadn't even made his debut when he severely damaged ankle ligaments playing a pre-season friendly at Brigg Town.
The Grand Baguette Diamond is valued at $1m (£800,000) and contains 761 diamonds - naturally, Cristiano Ronaldo owns one
Ronaldo wearing the Hublot 'Masterpiece' MP-09 Tourbillon Bi-Axis King Gold, the only one of its kind
Ronaldo owns a spectacular Rolex Daytona with a pearl dial is worth £605,000
Ronaldo wearing a sparkling silver Rolex GMT-Master II worth £392,000 in 2019
After a lengthy rehabilitation, he slummed it in non-league for a short time before quitting football to concentrate on building up his watch business.
Today he is based in Dubai, keeping a close eye on his Global Boutique on South Molton Street in central London.
Calliste added in his Sun interview: 'We sell watches, beautiful jewellery, and we have a certain amount of accessories, including Hermes bags.
'Having a Mayfair premises, with the amount of clients that walks in from around the world and the type of clients we attract, has been amazing for business.'
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