Eighth seed Raonic achieved his best career showing at the All England Club on Tuesday with a 4-6, 6-1, 7-6 (4), 6-3 fourth-round win over Japanese 10th seed Kei Nishikori.
Raonic becomes just the second Canadian to reach the Wimbledon quarter-finals in the Open era, which began in 1968.
He next faces Australian wild card Nick Kyrgios, who shocked second seed Rafael Nadal with a 7-6 (5), 5-7, 7-6 (5), 6-2 win later Tuesday.
Bouchard made her way there on Monday with a defeat of Alize Cornet. She will face off in the next round against German ninth seed Angelique Kerber, who upset fifth seed Maria Sharapova 7-6 (7-4), 4-6, 6-4, winning on a seventh match point.
Bouchard hammered Kerber in the French Open fourth round a month ago.
"The match against Bouchard will be a tough one," said Kerber. "I lost against her in Paris, but I'm feeling right now better and I'm feeling better on grass.
"I've never played her on this surface, so I will be focused like today just on myself."
Raonic laid down 34 aces in his victory over Nishikori, who is coached by former French Open winner Michael Chang. Raonic broke three times, saved five break points against his serve and ended with 64 winners in the comprehensive victory.
"I've been serving in general well this tournament, and even throughout the clay court season," said Raonic. "But obviously here it sort of gets exemplified a little bit more. It's a little bit more on display.
"That's helping me, taking a lot of pressure off me and putting more so on my opponents."
The 23-year-old from Thornhill, Ont., became the first Canadian to defeat Nishikori. The Japanese player had won his previous six matches against Canadians, including two against Raonic.
In men's doubles, veteran Daniel Nestor of Toronto and Serbian partner Nenad Zimonjic finished off a rain-delayed match from Monday as the third seeds reached the quarter-finals over Pablo Cuevas of Uruguay and David Marrero of Spain 7-6 (8), 6-4, 6-4.
Vancouver's Vasek Pospisil and American Jack Sock reached the third round over India's Rohan Bopanna and Aisam Quereshi of Pakistan 6-7 (3), 7-6 (5), 6-3, 7-5.
Raonic opened the match by losing his first service game, which allowed Nishikori to win the opening set in 39 minutes.
Raonic fought hard to come back. He broke twice in the second set to get back level at a set each, and won the third set on a tiebreaker.
Raonic earned a late break in the eighth game of the fourth set, then set up a match point with a service winner and advanced on his first opportunity a game later.
Raonic said he's not particularly impressed by the records he is setting in his career.
"To to this point there hasn't been as much Canadian success, especially on the singles side in the men's," he said. "You appreciate them, but you don't give them too much value because it's ambitions that are beyond doing what no Canadian has done before. It's about really trying to become the best player in the world."
Raonic said his serve will be key in his Wednesday quarter-final.
"I've been able to do that so far, it's what's going to put the pressure on my opponent," he said. "It's what's going to give me a bit of freedom on the return games.
"After that, the most important thing is going to be the attitude, the mental approach. I want to do much better than I did in Paris. I feel like I'm ready to do so."
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