Three-time champion Federer beat 20th seed Anderson 6-0 6-4 in a match lasting just under an hour and a half.
Fellow Canadian teen Denis Shapovalov, a 19-year-old from Richmond Hill, Ont., was scheduled to play the Friday evening semifinal against No. 4 seed Roger Federer of Switzerland.
The 20th seed booked his place in the last four with a 6-7 (5) 6-4 6-2 win over Frances Tiafoe.
The teenager will face defending champion John Isner after the American defeated Roberto Bautista Agut of Spain 7-6 (7-1) 7-6 (7-5).
Following Petra Kvitova's exit on Tuesday, Halep needs only to reach tomorrow's final to knock Naomi Osaka off the top of women's tennis after being deposed following the Japanese's second major win at the Australian Open earlier this year. "I wasn't able to do like all the other matches and just focus on what I had to do, and it really got to me too hard", he said. "Ashleigh is a good player, but I am excited for the final". "I just tried to impose myself from the start". "Today's match, I can be really happy with so I hope it's going to give me some confidence". That's just very tough to swallow'.
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The 32-year-old South African is yet to win a Grand Slam title, but his home advantage could play a factor on Thursday, and well as his period of rest ahead of the tournament. Conversely, Isner has played 11 Masters semi-finals, winning four, although only twice was he a pre-match favourite - once against Richard Gasquet in Toronto in 2012 and also against Filip Krajinovic in Paris in 2017.
Federer was Shapovalov's favourite player growing up and the Canadian said it will be a "dream come true" facing the Swiss legend.
Federer was seen playing with an attacking mindset, bringing his "A" game to the tennis court, displaying cheeky net skills and crafty slices from side to side.
Isner's power was evident on his first service of the sixth game when he handcuffed Auger-Aliassime and sent him stumbling to the right. However, Federer struggled in the following game to hold after he was trailing 0-40.
Anderson refused to buckle and when he finally managed to get on the board by breaking the former world number one's serve, he was sarcastically applauded by some sections of what was a predictably pro-Federer crowd. I think I will do at the end of the tournament.
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