His second one promises to be one he will never forget.
Levine defeated Belgium's Xavier Malisse 6-4, 7-6 (3) on Monday night to advance to the second round of the tournament, where the 25-year-old left hander will take on eight-time French Open champion Rafael Nadal.
Levine, who was born in Nepean, Ont., moved to Florida in his teens and played as an American until recently. He has faced Nadal once before, also in the second round of the 2008 Rogers Cup in Toronto.
"I remember I got off to a really, really good start," said Levine, who began playing as a Canadian in December. "I was up 4-1 in the first set. Then I was kind of sitting on the changeover. I remember kind of looking at the scoreboard and saying, 'There's something wrong about that.'"
Nadal fought off two break points and roared back for a 6-4, 6-2 win over Levine on July 23, 2008.
Levine had a rooting section behind him against Malisse on Monday night as family and friends made the two-hour drive from Ottawa to Montreal to see him on the court. But Levine said he's not exactly used to seeing so many familiar faces in the stands.
"It's a rare feeling to have family and friends there at a tournament because we travel all over the world playing different tournaments," he said. "Rarely is it so close to home so for me it was really special.
"The crowd was getting behind me at some crucial moments in the match. It was really nice. I can't imagine what it would be like to play on even the bigger court. Hopefully I'll get that feeling and it will help me out."
Levine can expect a larger crowd behind him when he takes on the 12-time Grand Slam champion Nadal Wednesday.
Levine is one of five Canadians remaining in the main draw after Peter Polansky became the first to fall out of the men's tournament.
Polansky, who qualified over the weekend, won the opening set of his centre-court match against ninth-seed Kei Nishikori of Japan before an enthusiastic crowd at Uniprix Stadium.
He took a 2-0 lead in the second set but ultimately fell, 4-6, 6-4, 6-2 in just over two hours.
"It's possible that's when my intensity dropped a little bit, almost like a sense of relief that I had an opportunity and it dropped just enough to let him back in," Polansky said.
Germany's Florian Mayer defeated Bernard Tomic of Australia, 5-7, 6-3, 6-3. Mayer will face top-seeded Novak Djokovic in the second round.
Milos Raonic, who is seeded 11th, will face France's Jeremy Chardy in one of four singles matches involving Canadians on Tuesday.
Vasek Pospisil takes on John Isner, the lone American in the main draw. Fellow Canadian wild-cards Frank Dancevic and Filip Peliwo will also play their first-round matches. Dancevic faces Taiwan's Lu Yen-Hsun and Peliwo takes on Jarkko Nieminen of Finland.
The six Canadians in the main draw were the most since 1987 when there were seven, including current Davis Cup captain Martin Laurendeau and Stephane Bonneau, one of four Quebec tennis players inducted into the Rogers Cup Hall of Fame prior to the evening's matches.
Pospisil won the Odlum Brown VanOpen final on Sunday. The 23-year-old Vancouver native fought off three match-point opportunities against Britain's Daniel Evans and rallied from a 1-4 deficit in the final set for a 6-0, 1-6, 7-5 win.
The hard-serving Isner also had a long week, losing to Juan Martin del Potro in Sunday's Citi Open final in Washington, D.C.
Pospisil admitted he had mixed feelings about opening against the 6-foot-9 Isner.
"He's also confident," Pospisil said. "Either way it's going to be extremely tough when you have a server like that, a dangerous player."