Both had to wait out a rain interruption lasting nearly five hours before taking comprehensive third-round victories to join Carling Bassett-Seguso (1983, 1986), Patricia Hy-Boulais (1996-97) and Daniel Nestor (1999) as Canadians who made it into the second week of a major.
Bouchard, semifinalist in Melbourne and Paris already this season, posted a 6-3, 6-4 defeat of German Andrea Petkovic.
Raonic, from Thornhill, Ont., joined Bouchard in Wimbledon's second week by beating Poland's Lukasz Kubot in the third round 7-6 (2), 7-6(4), 6-2. He fired over 30 aces and 50 winners, breaking twice with just six unforced errors on the way to victory.
"I was able to be dominant on my serve, I only lost nine points on it," said Raonic. "This definitely makes my life a lot easier and puts pressure on him.
"But at the same time, I didn't really have my opportunities. I played a few good points in tiebreaks and he was able to of hold on."
Raonic has won three straight Wimbledon grass matches for the first time, after doing the same at Halle, Germany in 2011 and 2012.
"I'm starting from very low comfort level on grass but now I'm feeling pretty comfortable," said Raonic. "I've made pretty significant progress on this surface this year."
The 13th-seeded Bouchard, from Westmount, Que., started her match in the early afternoon but found herself in the locker-room for nearly five hours after 15 minutes of play as rain wrecked the schedule.
But the weather cleared up in the early evening with Bouchard and Petkovic returning to the court with the Canadian leading 2-1.
Bouchard picked up where she left off, putting the pressure on a player who had defeated her in three previous meetings including the Rogers Cup in Toronto three years ago.
She took victory on her third match point when Petkovic hit the net with a return.
Bouchard produced 30 winners and 14 unforced errors, breaking five time in the match lasting less than 90 minutes.
She next plays France's Alzie Cornet, who beat top seed and five-time champion Serena Williams for the second time this season, winning 1-6, 6-3, 6-4 in a stunning upset. Cornet won their previous meeting on clay at Strasbourg last year.
"I played well, even though it was straight sets it was a battle," said Bouchard. "It was tough with the lone rain delay, but it was the same for both girls
"I'm happy I was able to close it out with any serve, being aggressive and taking the ball early. During the rain delay I tried to conserve energy — I wanted to give it all on the court.
Bouchard said she didn't actually mind the wait.
"Rain is part of the Wimbledon expedience," she said with a laugh. "We've been lucky so far, you have to have some rain at Wimbledon."
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