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Nearly 15 years ago (!!!), an 18-year-old named Milos Raonic, ranked No. 679, qualified for his first career ATP Tour main draw at the 2009 Rogers Cup in Montreal.

It was only his second ATP-level tournament, having received a wild card into the same event in Toronto the previous year, and losing in the first round of qualifying.

This time, after squeaking through the very solid Teymuraz Gabashvili (ranked No. 77) in the first round 6-7 (7), 6-2, 7-5, he came out the next day and played tough French lefty serve-volleyer Michael Llodra for a spot in the show.

Llodra might not physically have been at 100 per cent that day, if memory serves. But it was far tougher for the 18-year-old kid to turn the page on a massive win the previous day, and come out against completely different type of player, with so much more at stake.

Raonic won, 6-4, 7-6 (3).

He was, to say the least, over the moon.

The most noticeable thing about his game back in those days is how much simpler his service motion was. There was little of that raising of both his arms up high in front of him, before going into the toss and contact.

Here’s what it looked like (the video was rescued from a long-forgotten Photobucket account, and so it’s a bit dodgy. Still, fun to watch).

Here’s what Raonic had to say afterwards in the press conference, with the challenge of world No. 10 Fernandez Gonzalez of Chile facing him in the first round.

That match was off the charts, on the Grandstand court. The fans were massively behind Raonic, much to the annoyance of Gonzalez. And in the end, the Chilean barely pulled it out, 6-4, 6-7 (6), 6-4.

After that, Raonic headed directly to Thailand to play a series of $10,000 tournaments (those no longer exist, that rock-bottom purse having been raised to $15,000). After saying in press he needed to focus on playing his own game, and not on some level drop down to the level of his opponents in lower-level events, that’s exactly what he did.

Raonic went 12-2 on the trip with a title, a final and a semi. By the time he came back to North America a month later, he was inside the top 400.

Earlier that year, in Montreal …

Five months earlier in March, 2009 – also in Montreal but inside the building next to the Rogers Cup stadium before family and friends, Raonic was ranked No. 804 and playing a Futures event.

He won that one.

Here’s Raonic in the first round, playing a 24-year-old American named Robbye Poole who was trying to make it to the pros after starring at the University of Mississippi.

Raonic beat him, 6-3, 6-4.

Five years on from that day, Poole was a hitting partner for Serena Williams. And later he worked with Genie Bouchard for a few months. He now sells commercial insurance in south Florida.

It’s hard to know what the future holds for Raonic, who withdrew from the tournaments he entered in Asia and Europe, and has committed to the exhibition UTS event next month.

But back in those days, despite the big serve, it was still hard to fathom that a kid from Thornhill, Ont. was going to end up having the career he’s had.