Shapovalov, playing with Rohan Bopanna, is set to face Nick Kyrgios and Matt Reid in the doubles semifinals of the Stuttgart ATP 250 on Saturday.
Raonic, meanwhile will take on another Canadian in the singles semis, in Felix Auger-Aliassime, who defeated Dustin Brown in three tiebreaks in the quarterfinals.
Perhaps Canada will be taking home even more titles come Sunday.