Even while slumping to a shock loss on the Challenger Tour in 2005, Andy Murray always seemed destined for greatness.

Then 18, it would be the Brit's final year – his first as a professional – on the ATP's second-tier circuit.

Murray had already reached the third round at Wimbledon, pushing David Nalbandian in a five-set loss, and started to shine in Challengers, winning the only two titles of his career at that level in 2005. Mons would be the location of his last appearance in Challengers, having won the title in Binghamton in August after a shock quarter-final defeat in Vancouver the week prior.

There was no looking back for Murray. Just three years later, he was a US Open finalist, and New York would be the scene of his first major success in 2012.

That Murray would go on to enjoy a storied career – which is set to end in 2019 – was perhaps still in some doubt when he lost to Paul Baccanello in Vancouver nearly 14 years ago, but there was no question in the Australian's mind.

Asked if he saw Murray achieving what he has, Baccanello, with no hesitation, told Omnisport: "Yeah, yeah.

"When I played and won the match, I was like, 'That's a pretty good win, this guy is going to be a great player'. You could tell at that stage. At the time, he was really up and coming, everyone was talking about this guy, Andy Murray from Britain.

"Mark Petchey – he was coaching him at the time – I saw him later on, he said, 'That's going to be a scalp you'll be talking about for a long time' and here I am, 20 years later, talking to you about a match that I played against one of the greatest players to play the game so really lucky. He was always going to be good."

After winning three grand slams and two Olympic gold medals as part of 45 ATP titles, as well as a Davis Cup crown, Murray will exit the sport as a great among a generation of them, his first-round exit in Melbourne on Monday likely marking his last appearance at the year's first major.

A superstar baseliner with every shot in his repertoire, Murray was already producing shocks the year after his meeting with Baccanello, beating Andy Roddick twice and stunning Roger Federer in Cincinnati.

"At the time, his forehand was a little bit more predictable, he'd just hook it cross-court, hook it cross-court," Baccanello, now a physio and developer of Tennisphere, says. "He didn't have that long-line forehand that really made him into a really good player.

"His backhand was ridiculous how solid it was, I could probably count on one hand how many errors he made on that side the whole match. Amazing talent. First serve was great and at that stage, the things that were probably in need of improvement were a little bit of variety in his forehand and his second serve and obviously he fixed those and became the player he was."

Alongside Federer, Rafael Nadal and Novak Djokovic, Murray – whose troublesome hip is set to end his career – helped form one of the most dominant eras in men's tennis.

Baccanello also faced a 17-year-old Nadal in Segovia in 2003 – losing 7-6 (7-2) 6-4 in a semi-final – and said it was obvious what separated the greats from the rest.

"They just make balls that most guys don't. They read the play," he said.

"And the big one was, for me, these guys actually thrived on pressure situations and that was something that I didn't do and I was an older player and didn't do it as well as these guys when they were 18, 19 years of age."

Still, Baccanello can look back on his win over Murray in Vancouver, the last time the former world number one suffered defeat in a completed match on the Challenger Tour. His own career cut short by injury, Baccanello came from a break down late in the third set for a 2-6 7-5 7-6 (7-2) victory. Murray would not lose to an Australian again for almost 12 years – a run of 18 victories.

"In a nutshell, I couldn't have really played any better. I think he was a little bit off," he said. "He served for it in the third set, I got a bit lucky on a couple of returns and actually played a pretty good third-set tie-break. In a nutshell, that's pretty much what happened.

"The serve was probably my strong suit and trying to break him down on my serve, he had an unbelievable return, it was pretty challenging to hold serve for the whole match and somehow at the end I just found a couple of serves that I needed and that's really what got me over the line."

Even with a win he remembers fondly, Baccanello had little doubt where Murray would end up, and he was right.