2023 Australian Open Semifinals Betting Picks, Odds, Predictions and Tennis Best Bets: Djokovic vs. Paul, Tsitsipas vs. Khachanov

This article is part of our Tennis Picks series.

The men's semifinals of the Australian Open will be played Friday in Melbourne, which is Thursday night in America. Novak Djokovic is two wins away from tying Rafael Nadal for the most men's singles Grand Slam titles all time with 22, but he could have his hands full with an American who has notched his fair share of major victories recently. Stefanos Tsitsipas is in the Aussie Open semifinals for the fourth time in five years, but he has been denied at this stage on three previous occasions. Can he get over the hump against an opponent that's making his second consecutive Grand Slam semifinal appearance?

All Tennis Odds & Lines are taken from DraftKings Sportsbook, but you can sometimes find more favorable odds on some of these matches by checking mobile sportsbooks such as FanDuel Sportsbook, BetMGM, Caesars Sportsbook, or any of the other best sports betting siteslaunched in Ohio.

Men's matches at Grand Slams are best of five sets, requiring a greater amount of physical stamina and mental fortitude than other ATP Tour events. All four remaining players have proven adept at winning extended matches in these hot hard-court conditions, but a mix of previous hard court results, recent form and stylistic matchups can help predict how the upcoming matches will unfold.

Novak Djokovic (-1800) vs. Tommy Paul (+1000)

It isn't hard to see why oddsmakers give Paul almost no chance in this one. In addition to his 22nd Grand Slam title overall, Djokovic is going for his 10th at the Australian Open. He hasn't lost a match here since 2018, and Djokovic's opponents at this year's tournament have won an average of only 8.4 games per match. While Paul could be a bit overwhelmed by the moment, Djokovic is locked in and has been here plenty of times before.

Paul has all the tools to hang with anybody, and the 25-year-old American has started to put the whole package together with some impressive results over the past few months. While this is easily his deepest foray into a Grand Slam, Paul can draw confidence from recent hard-court wins over Carlos Alcaraz in August and Rafael Nadal in November as he prepares to face Djokovic for the first time. If Paul comes out hot in the biggest match of his career to date, he could take one of the first two sets and make a match out of this.

Prediction: Djokovic in four sets

Stefanos Tsitsipas (-250) vs. Karen Khachanov (+205)

In addition to his 0-3 semifinal record at the Australian Open, Tsitsipas has a 1-1 semifinal record at the French Open, so he knows he's capable of winning in this round. The No. 3 seed has played plenty of big matches late in tournaments, and as far as opponents go, Khachanov is a step down in level of competition from the names Tsitsipas has usually faced at this stage. The only player to take a set off Tsitsipas so far here was Jannik Sinner, who battled back to force a fifth set after Tsitsipas won the first two. Given his superior ranking and 5-0 head-to-head edge against Khachanov, Tsitsipas has to fancy his chances of setting up a rematch of the 2021 French Open final against Djokovic.

Khachanov is two years older than the 24-year-old Tsitsipas, but the Russian has finally gained the belief that he can contend deep in Grand Slams. After falling in the fourth round or quarterfinals seven times in his first 22 Grand Slam appearances, Khachanov reached the semifinals of the 2022 US Open and is right back at this stage again in the next Grand Slam. Khachanov also has a silver medal at the 2021 Olympics under his belt, so he's proven he can hold his own when the stakes are highest. Like Tsitsipas, Khachanov has dropped only two sets in this tournament, and this is a better version of Khachanov than the one who lost the previous five meetings to Tsitsipas.

Prediction: Tsitsipas in five sets