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2023 Wimbledon Men's Semifinal Picks & Best Bets for Djokovic-Skinner, Alcaraz-Medvedev

Isla Knightley for Bookies.com

Isla Knightley  | 6 mins

2023 Wimbledon Men's Semifinal Picks & Best Bets for Djokovic-Skinner, Alcaraz-Medvedev

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The gentlemen’s semifinals at the All England Club are shaping up to be classics with the crème de la crème of the men’s game set to do battle in two mouthwatering matchups on Friday, July 14.

First up, the seven-time Wimbledon champion Novak Djokovic will face NextGen star Jannik Sinner in the day’s opening semifinal. Then, World No. 1 Carlos Alcaraz and former World No. 1 Daniil Medvedev will bring down the curtain on Centre Court in the day’s second semifinal.

Who will advance into Sunday’s final? Will it be the matchup that everyone is hankering after: Djokovic vs Alcaraz? Or might there be a tennis betting upset in one or the other or both semifinals? [Insert dramatic shiver].

As ever, we’re on top of the action here at Bookies.com, bringing you daily predictions and tennis picks from the world’s oldest and most prestigious Grand Slam. So, let’s dive straight into our Wimbledon Day 12 Predictions and picks, complete with tennis odds from a stable of trusted sportsbooks.

Novak Djokovic vs Jannik Sinner

There is probably nothing more challenging in tennis than attempting to beat World No, 2 Djokovic in the best-of-five sets scenario of a Grand Slam. 

World No, 8 Sinner knows this only too well and what it means to go to battle with one of the game’s greats. Why, last year, on these very same iconic lawns, Sinner was well on his way to orchestrating one of the biggest upsets of the tournament in the quarterfinals – until he wasn’t.

The Italian was up two sets before Djokovic turned the tables on him, roaring back to clinch the 5-7, 2-6, 6-3, 6-2, 6-2 win. And just like that, it was Sinner leaving London instead of Djokovic. Now, a year later, the 21-year-old Italian has come full circle to face Djokovic again in Wimbledon. The stakes are higher this time around, the prize greater with a spot in the Wimbledon final on the line.

Djokovic is the ultimate “Big Match” player. He’s played more big matches on the game’s biggest stages than most and he thrives in these kinds of situations whether he is the favorite or the underdog on sports betting apps.

Of course, in this case, the markets heavily favor Djokovic over Sinner to win, and few would bet against him either now that he knows what to expect from the Italian after their first grass encounter. 

Then, there is the small matter of earning more accolades at SW19 inspiring Djokovic. The potential to win an eighth Wimbledon title (to tie Roger Federer’s record), 24th Grand Slam title (to tie Margaret Court’s record) and keep his bid for a Calendar Slam alive (a feat last accomplished by Steffi Graff in 1998). 

Having said all that the potential for the upset remains very high here. In fact, there is a strong feeling that Sinner could absolutely win this match, though it is a longshot bet not suited for the fainthearted.

Sinner was always the dark horse in Djokovic’s path to the final, the one player that had the most legitimate shot to derail him from his historical quests in Wimbledon. 

That fact hasn’t changed at all. He’s got the game on grass. He has looked very solid during his run, dropping just two sets in five matches to reach his first-ever major semifinal. While Djokovic hasn’t looked very sharp lately, dropping a set in each of his last two matches, including the first set to Andrey Rublev in the quarterfinals. 

Most pundits will agree that this is going to be Djokovic’s toughest test, many of them predicting a four to five-set match. But we’re going the whole hog and predicting the outright upset! Yup, you heard it here first!

Wimbledon Best Bet: Sinner To Win +430 at FanDuel

Carlos Alcaraz vs Daniil Medvedev

World No. 1 Alcaraz and World No. 3 Medvedev emerged from a stacked top-half of the draw, falling in line with their top seeding to set up a semifinal showdown that many had circled ever since the draw was first released.

This is their third-ever meeting and second at Wimbledon. In 2021, Medvedev easily beat the then 18-year-old Alcaraz 6-4, 6-1, 6-2 in the R64. That was then, however. The same year Medvedev went on to win the US Open, defeating Djokovic in straight sets in the final. 

Since then, Alcaraz went on a meteoric rise in the ATP rankings, rocketing  to the top of the standings on the back of winning the 2022 US Open title. Earlier this year, he levelled the score with Medvedev, beating the Russian 6-3, 6-2 in the Indian Wells final to claim his fourth ATP 1000 Masters title. 

Though the Spaniard is merely 20 years old, he’s a total revelation, achieving more than most have at such a young age. He’s often compared to his illustrious compatriot Rafael Nadal, but he is possibly more dynamic as an all-surface player than Nadal was early on his enviable career. 

Alcaraz has had the tougher path into the final four, having to overcome former Wimbledon finalist Matteo Berrettini in the R16 and then Holger Rune in the quarterfinals, 7-6 (3), 6-4, 6-4. 

Whereas Medvedev has had a relatively easier path, avoiding any seeded threats up to this point. Though he was made to work for it by surprise quarterfinalist Chrstopher Eubanks, going the distance to clinch the  6-4, 1-6, 4-6,  7-6 (4), 6-1 victory.

It is not surprising to see the market the way it is, nestled rather delicately between them with tennis odds that suggest a close matchup that could go either way. Both are championship-pedigreed players that are enjoying standout seasons. But both are also making their first-ever Wimbledon semi-final appearance.

That said, Alcaraz is the favorite and the vogue tennis pick among the punditocracy. Most are backing the Alcaraz to advance into the final, and following Medvedev’s scare against Eubanks, the edge does tip in the Spanish phenom’s favor indeed.

Wimbledon Best Bet: Alcaraz -250 at BetMGM

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About the Author

Isla Knightley for Bookies.com
Isla Knightley
Isla, a sports journalist and betting expert, covers several sports, including the NFL, as well politics. She joined Bookies.com in 2021 after contributing to other betting sites.