The former top-ranked American defeated Raonic 6-4, 4-6, 10-7 in the Sport Chek Face-Off exhibition match on Friday night at Air Canada Centre.
When Roddick — known as much for his humour as his short fuse — wasn't working the crowd like a seasoned pro, chatting with courtside fans between points and banging his racket against the net in mock anger, he was rallying with two breaks from down 3-1 to win the first set.
"I hope not," Raonic responded when asked if Roddick might consider a comeback.
Roddick, who retired at this year's U.S. Open, had the crowd of 6,558 in hysterics in the second set as he imitated fellow tennis stars, such as Maria Sharapova's interminable serve, Rafael Nadal's familiar clothing rituals and Novak Djokovic's dexterity.
Raonic looked on in amusement but didn't take any heat off his feared serve, pulling ahead 5-3 in the second with a blazing ace. The Texan could only shrug his shoulders after the ball zipped by his head.
With the audience chanting for Raonic in the 10-point super-tiebreak, Roddick impressed with a down-the-line drop shot that put him up 9-6.
Roddick, huffing and puffing early in the first set, jokingly called for a timeout to collect his breath. Before the match, he said his fitness regiment since retiring at this year's U.S. Open has been less than stringent.
"What kind of shape am I in now? Well round is a shape," said Roddick with a laugh. "I had a very detailed retirement plan, and I feel like I've met every aspect of it: a lot of golf, a lot of carbs, a lot of fried food, and some booze, occasionally — I've been completely committed ... The results have shown."
The only prior meeting between the two was in the 2011 Memphis final where Roddick defeated the now No. 13-ranked Raonic of Thornhill, Ont., in three sets. That tilt produced a YouTube-worthy moment when Roddick won the title with an incredible diving forehand on match point.
The two have often been compared to each other mostly for their powerful serves.
"I like his game and I equally like the way he goes about his business," said the 30-year-old Roddick of his 21-year-old opponent. "He's very diligent and he has the hunger to get better and not be satisfied, which will serve him well."
For Raonic, Friday's event was about growing the game in Canada and from his viewpoint the sport is on the right track in this country.
"There's a lot of support, a lot of appreciation and interest in Canadian players, especially during Davis Cup," he said. "I think the kind of support we're getting there is really amazing. It's something we want to keep building up."
The exhibition also featured 15-time Grand Slam champion and world No. 3 Serena Williams taking on world No. 4 Agnieszka Radwanska in a rematch of this year's Wimbledon final, albeit with the stakes decidedly lower.
Radwanska took advantage of Williams' disinterested start to break twice and jump out to an early 4-0 lead. Williams finally put some heat in her strokes in the fifth game, but it wasn't enough as she dropped behind 5-0.
Williams woke up to win four straight games but Radwanska took the first set 6-4 on a sizzling backhand that her opponent opted not to chase.
En route to a 3-2 lead in the second, Radwanska earned ample cheers from the fans when she hit a between-the-legs shot that Williams returned into the net.
Radwanska aced on match point to earn a small measure of revenge for Wimbledon, defeating Williams 6-4, 6-4.
The loss is unlikely to linger long with Williams, who is coming off one of the best seasons in her career. After a slow start, she won slam titles in both singles and doubles at Wimbledon, gold in singles and doubles at the London Olympics, a U.S. Open title and the WTA Championships last month. She also collected titles this year in Charleston, Madrid and Stanford.
The 31-year-old says she's pleased with her season but isn't the type to dwell on what went right.
"I'm not a bit reflector," said Williams. "I always feel like I want to do more, I want to improve. Once you start reflecting ... you can become really satisfied. For me, I'm always trying to do a bit better. I'll have more time to reflect after my career."
Radwanska, a 23-year-old native of Krakow, Poland, won this year at Dubai, Miami and Brussels before reaching the final at Wimbledon.
"It was a pretty good match. I was just happy I could play three sets against a grass tennis killer," said Radwanska of her Wimbledon date with Williams.
The evening kicked off with a light-hearted mixed doubles match between Team Canada — Raonic and Radwanska — against Team USA's Roddick and Williams.
The foursome were joined by an inter-changing mix of celebrities, including CBC personality George Stroumboulopoulos, Adrian Grenier of the HBO show "Entourage," "Bachelor" star Brad Smith and CFL commissioner Mark Cohon. All proved to be willing sports, though clearly of limited skill with a racket.