It’s been a weird road to the Wimbledon Final for Jannik Sinner.

The entire tennis world wondered how the Italian would recover after choking away the French Open title to Carlos Alcaraz, and those concerns only grew louder when Sinner lost to Alexander Bublik in the second round at Halle.

Sinner eventually quieted the skeptics by winning his first nine sets at Wimbledon, but then things got funky against Grigor Dimitrov in the Round of 16.

Dimitrov took the first two sets of that match, and there were concerns about Sinner’s elbow after he fell on it early in the contest. 

Then, Sinner caught the biggest of breaks when Dimitrov injured himself and had to retire from the match despite being up two sets to none.

Sinner advanced, but there were questions about his health and, if he was fit to play, how he would respond to a very strange victory against Dimitrov.

It turns out that Sinner was fine, and he dominated Ben Shelton in the quarterfinals, 7-6, 6-4, 6-4, meaning the only sets he’s lost at Wimbledon were the two against Dimitrov.

He now sets his sights on Novak Djokovic in Friday’s semifinal.

Player	Odds
Novak Djokovic	+162
Jannik Sinner	-200

Sinner has won four matches in a row against Djokovic, including a straight-set victory at the French Open, but there are more questions about the 23-year-old’s fitness right now than the 38-year-old.

Djokovic needed to get through the first five rounds unscathed and fresh to have a chance in this match, and he did just that. The Serb has only lost three sets during Wimbledon, and he hasn’t needed to go the distance yet in any match.

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We should be getting the best version of Djokovic, whatever that may look like at this point in his career, on Friday.

As for Sinner, he looked like himself against Shelton, but he was hardly put through the paces as the American couldn’t make any hay against the serve. 

That won’t be the case against Djokovic.

A couple of days ago, you’d say that a long match would favor the younger Sinner over Djokovic.

But after watching Sinner go down against Dimitrov, you wonder if his elbow would hold up over the course of what would be a grueling test against Djokovic.

Djokovic will know that he needs to make this a marathon, and I like his chances of doing that in front of what should be a raucous crowd.

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Michael Leboff is a long-suffering Islanders fan, but a long-profiting sports bettor with 10 years of experience in the gambling industry. He loves using game theory to help punters win bracket pools, find long shots, and learn how to beat the market in mainstream and niche sports.