Raonic and Bouchard advanced to the fourth round, setting up Monday matches a day ahead of their July 1 national holiday.
Raonic became the first Canadian to advance to the final 16 in the Open era at Wimbledon since Daniel Nestor in 1999 with a 7-6 (2), 7-6 (4), 6-2 win over Lukasz Kubot of Poland.
Bouchard, the first Canadian woman since Patricia Hy-Boulais in 1996-97 to advance to the fourth round, beat Germany's Andrea Petkovic 6-3, 6-4.
Eighth-seeded Raonic and 13th-seeded Bouchard played simultaneously, and had to endure about a 4 1/2-hour rain delay.
For complete Wimbledon coverage, including updated draws and reports from Steve Tignor, head to our tournament page.