Young Canadian Felix Auger-Aliassime will try to spring a major upset on Friday when he faces second-seeded Daniil Medvedev in the men's singles semifinals at the 2021 U.S. Open. The 21-year-old Auger-Aliassime advanced after Carlos Alcaraz retired, and he has struggled to win in big matches so far. Medvedev, meanwhile, is the second-ranked player in the world and has more than held his own against the world's top players. On paper, it's a mismatch, but Auger-Aliassime is looking to take his next big step. The match is set to begin at 3 p.m. ET.

The latest Auger-Aliassime vs. Medvedev odds from Caesars Sportsbook list Medvedev as the -600 favorite (risk $600 to win $100), while Auger-Aliassime is the +400 underdog. The over-under for total games is set at 35.5. Before you lock in any Medvedev vs. Auger-Aliassime 2021 U.S. Open men's semifinals picks, you need to check out what expert Sean Calvert has to say.

Calvert is the renowned handicapper who called Stan Wawrinka winning the 2014 Australian Open at 60-1, the last Australian title won by someone other than Novak Djokovic or Roger Federer. In 2019, Calvert took down a huge score on Dominic Thiem winning Indian Wells at 80-1. 

And earlier in 2021, he nailed both of his bets for the Wimbledon men's singles final: Djokovic to beat Matteo Berrettini three sets to one (+275) and Djokovic to win and both players to win a set (+130). Anyone following his picks is way up.

Now, Calvert has been digging deep into the latest 2021 U.S. Open odds and released his coveted best bet for Medvedev vs. Auger-Aliassime. He's only sharing his expert U.S. Open picks and analysis at SportsLine.

Felix Auger-Aliassime vs. Daniil Medvedev preview

Medvedev has come a long way since these players' only head-to-head meeting, at the 2018 Rogers Cup. Auger-Aliassime took the first set of that match, but the Russian won the third on a 9-7 tie-break, and the 25-year-old has since been to two Grand Slam finals. This is his third straight semifinal at the U.S. Open, and Medvedev will be motivated to finally break through. Auger-Aliassime is just 3-10 in matches against the world's top five players, while Medvedev has won six of his 10 matches against the world's best. 

Medvedev should be more rested, as he was the first player to advance and has had two full days to recover. Auger-Aliassime didn't have to play a full match in the quarters, but he played two four-set matches and a five-setter in the first four rounds. Auger-Aliassime has broken serve just 17 percent of the time at this tournament, while Medvedev is at 41 percent. The Russian will be happy to swap rallies from the baseline, and Auger-Aliassime might not have the experience to challenge him any other way.          

How to make Auger-Aliassime vs. Medvedev picks

Calvert has broken down the latest U.S. Open men's quarterfinals odds and released a best bet that returns almost 3-1. Calvert's U.S. Open picks are only available at SportsLine.

Who wins Medvedev vs. Auger-Aliassime in the 2021 U.S. Open men's semifinal? And what best bet do you need to be all over? Visit SportsLine now to see Sean Calvert's best bets for Auger-Aliassime vs. Medvedev, all from the famed tennis handicapper who called Wawrinka winning the 2014 Australian Open at 60-1, and find out.