Karen Khachanov vs Alex Michelsen Tips, Prediction & Live Stream - Michelsen backed for upset & first Masters 1000 semi-final

Michelsen doesn't get the same plaudits as some of the other rising stars in the sport, but the 20-year-old is the second-youngest player in the top 50 and deserves to be talked about in the same breath as the likes of Jakub Mensik and Joao Fonseca. The American has been building nicely over the last couple of years and is on the cusp of breaking into the top 30 following his brilliant run to the Canada Masters quarter-finals. Meanwhile, Khachanov is trying to return to his best tennis after a difficult last couple of years, snapping a 11-match losing run against top 20 players when he defeated Casper Ruud in the R16.

I love Michelsen at $2.80 odds here. The American absolutely destroyed Khachanov in straight sets in their only previous meeting at the Australian Open earlier this season - they have very similar game styles, but Michelsen is a more contemporary, powerful and robust version. It's obviously too early to tell if this is a bogey matchup for Khachanov, but I feel this is close to a 'Pick Em' match, so very happy backing the underdog in Michelsen at those odds.

As mentioned, Michelsen leads 1-0, cruising past Khachanov 63 76(5) 62 in the third round of the Australian Open at the start of the year.

Khachanov has registered a 25-16 record on the season, coming into this contest at a steady No. 16 in the world.

It's been a decent season for Khachanov, but he's been lacking a deep run in the meaningful tournaments, which of course wasn't helped by an 11-match losing streak against top 20 opponents.

That's all changed at the Canada Masters this week, where he's a two-time former semi-finalist, compiling a 14-6 record at the event.

Khachanov has been fortunate to receive a kind draw, taking out a pair of qualifiers in Juan Pablo Ficovich and Emilio Nava before running into the best top seed he could have hoped for in an out-of-form Casper Ruud, taking out the eighth seed 6-4 7-5 after coming back from 2-4 down in the second set.

Michelsen has put together a 21-18 record on the season as he continues to establish himself on the main tour - and he's done a great job of avoiding 'second-year syndrome' so far in 2025.

Even though a maiden ATP title still eludes him, Michelsen has achieved some solid results, notably reaching the R16 of the Australian Open, winning the Estoril Challenger and making the semi-finals of Mallorca.

The 20-year-old continues to break new ground, reaching his first Masters 1000 quarter-final in Toronto this week.

Michelsen started off his run by beating Tomas Barrios-Vera in straight sets before taking the scalp of third seed Lorenzo Musetti 3-7 7-6 6-4. Michelsen then avoided a letdown, easing past countryman Learner Tien 6-3 6-3 in the R16.