Cracked Racquets: 2021 Wimbledon Quarterfinals Betting Guide

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With justifiable reasoning, many Americans consider the Post-July 4th to Labor Day stretch to be the doldrums of the professional sports calendar.

NFL Training Camps remain about a month away from their start date, college football has yet to begin, the NBA Playoffs are (normally) in the rearview mirror, many of the Major Pro Golf events have passed, the NHL season is done, and quite frankly, baseball is baseball. Additionally, without actual new competition to enjoy, much of the offseason team hopping/free agency schadenfreude/speculation content that fills the summer months can remain entertaining for only so long.

However, for both American tennis fans and opportunistic gamblers (groups in which there is much overlap), the July to September stretch represents a peak moment in the sporting season.

The month is generally kicked off by Manic Monday at Wimbledon, a day that sees sixteen of the best women’s and men’s tennis players in the world compete for a spot in the prestigious event’s Quarterfinal Round. Following Wimbledon’s conclusion, the tours immediately transition to the American Hard Court Summer Events, guaranteeing two consecutive months of action that can be enjoyed from sunrise to (oftentimes wayyyy past) sunset throughout the country.

With that said, while much exciting tennis lies in the weeks ahead for the professional tennis world, the action already heats up tomorrow in London as Gentlemen’s Singles quarterfinal play begins at Wimbledon

Top-seeded Novak Djokovic, winner of the year’s first two Grand Slam Singles titles, enters the round as the consensus pick to capture the tournament’s title (-182 title odds via Fanduel). He enters his quarterfinal match with a 31-3 (.912) overall record in 2021, and is comfortably favored (-5000 moneyline) over his opponent, first-time slam quarterfinalist Marton Fucsovics.

Sixth-seeded Roger Federer, who reached a record-extending 18th (!!!!) Wimbledon Quarterfinal on Monday, will face his toughest test of the tournament yet in fourteenth-seeded Hubert Hurkacz. The 24 year-old Polish player won his first Masters 1000 title earlier this year in Miami, and played some fantastic tennis to overcome a two-sets-to-one deficit and knock off second-seeded Daniil Medvedev in the fourth round. Matchups between Matteo Berrettini/Felix Auger Aliassime and Denis Shapovalov/Roberto Bautista Agut round out Wednesday’s battles, and set up what should be a fantastic day of tennis on the grounds in London.

With that in mind, here are my picks for Wednesday’s Gentlemen’s Singles Quarterfinal matches at Wimbledon. To catch up on everything that has happened of late in the tennis world, or to start following along with the day-in, day-out happenings on tour, be sure to check out all of the work being done at

Small Citation note: Elo-Ratings, referred to repeatedly throughout this article, rank players based on who they beat and lose to, as well as the quality of the match scoreline. This differs from the ATP/WTA ranking systems, which rewards points to a player solely based on what round of a respective tournament he or she reaches, regardless of the quality the opponents he or she defeated to get there. As an example: To Elo-Ratings, a first-round victory over the fifth-ranked player in the world is more valuable than a quarterfinal-round victory over the #40 player. The opposite is the case for the ATP/WTA Rankings.

Also, unless otherwise noted, all stats come from, truly the best research database for anyone aspiring to wager successfully on pro tennis.

Hubert Hurkacz (+195) over Roger Federer: 0.50 units to win 0.98

Some of you may see this pick and immediately feel an inclination to click out of this article. After all, what sort of competent, credible analyst would pick against the winningest player in Wimbledon’ history at freaking Wimbledon?!

I understand that urging, however I humbly request that you allow me to make the Hurkacz case.

24 year-old Hubert Hurkacz’s physical characteristics and broad skill set very much embody the future of the game in men’s tennis. Standing at 6’6, he possesses the flexibility of a used-car salesman, the craftiness of a 5’10 point guard, the first step of a parent seeing their young child falling out of their high-chair, and the rubber right shoulder of MLB HOFer David Wells.

After winning his first Masters 1000 title in Miami, then losing six consecutive matches across the months of April, May, and June, Hurkacz has dropped just two sets in his four wins at Wimbledon this week. He ranks third amongst remaining players in the event with an 81% win percentage on his first serve points, and has been broken just three times in the tournament (each came against Medvedev in the 4th round).

According to Tennis Abstract’s stats leaderboard, Hurkacz ranks 17th in Hold % amongst Top 50 players (83.2%). While that number trails Roger Federer (ranked 8th, 86.5%), Hurkacz leads Federer in both Ace % (12th vs. 18th) and 1st serve win % (20th vs. 23rd), and has demonstrated the ability to hold serve at an elite level when playing his best tennis.

While Hurkacz’s statistics as a returner will require improvement moving forward, he currently leads Federer in Brk % (44th to 46th), win % against 1st serves (36th vs. 45th), win % against 1st serves (40th vs. 46th), and % of return points won per match (41st vs. 48th) amongst Top 50 players. These numbers reflect the aggressive mentality both players demonstrate with their returns of serve. They also indicate that, in all likelihood, tomorrow will feature a serve-fest on center court.

For Federer in particular, his return of serve statistics demonstrate his recognition of the need to avoid playing long, physical rallies, as well as his faith in his own ability to hold serve. Federer’s played just twelve matches since the ATP Tour’s resumption in August. Though that number remains too small of a sample size to provide any conclusive evidence about the state of Federer’s game, the metrics are not kind to the soon-to-be 40 year-old. 

Federer’s break % in 2021, currently at 16.5%, is the lowest number of his career, and is only the second time ever that he’s been under a 20% mark. The other season that happened? 2000!!!!

Additionally, Federer’s first serve win percentage, ace percentage, percentage of serving points won, percentage of return points won, and percentage of total points won are all either at their lowest point since 2000 or lower than they’ve ever been in his career.

Coming off of multiple surgeries in the past few years and approaching his 40th birthday, some statistical decline could always be expected from Federer this season. He’s played fewer than 25 matches in the past two years, and clearly makes a more concerted effort now to conserve energy throughout the course of his matches. And, though his anticipation and footwork remain as impressive as ever, Federer seems to have finally lost that first step that made his lack of truly elite foot speed nearly unnoticeable throughout the prime of his pro career.

And that, my friends, is where Hubert Hurkacz comes back into play. Hurkacz possesses the weapons, aggressiveness, creativity, length, physicality, and serving prowess to give this version of Roger Federer all sorts of problems in tomorrow’s match.

When playing his best, Hurkacz possesses the ability to hit short angles, go flat down the line, absorb and redirect pace, incorporate slice, deploy the drop shot, and comfortably put away volleys, all within the span of the same point. Hurkacz looked excellent coming forward to the net in his win over Medvedev. He utilized serve-and-volley tactics whenever Medvedev returned from 12 feet behind the baseline, and moved forward almost every time Medvedev left a rally ball short in the court.

While Hurkacz’s return numbers are not great, he possesses both the requisite length and finesse to put the majority of his returns in play. If he can find the Federer backhand with his return (easier said than done), he should be able to create some opportunities for himself to break serve. Also, should any set reach a tiebreaker, Hurkacz also has the gumption (though sometimes it turns into hubris) to go down swinging. Against Roger Federer, that sort of aggressiveness is an absolute must.

Hurkacz must employ each of his skills against Federer tomorrow, and do his best to keep Federer on his back foot. Additionally, he must continue to experience the same success on serve that he has thus far in the event. If he’s able to so, a pathway to his first career Grand Slam semifinal should certainly be there for Hurkacz

In summary: Hurkacz’s game is tailor made for modern grass court tennis, for the first time in his life Federer (almost, sort of) looks his age, the concept of him winning a slam at age 39 would break my brain, and Hurkacz is just ballsy enough to pull this sort of victory off. I’m only comfortable throwing half a unit on it, but give me Hurkacz to pull off the upset at +195 odds. 

Over 3.5 sets in Hurkacz/Federer: -180, 1.00 units to win 0.56

All of that said, I am 99.999999999% confident that Roger Federer will not lose this match in straight sets.

In his 118 career matches at Wimbledon, Federer has lost just two of them in straight-sets. And, for the record, those two losses happened back in 2000 and 2002 respectively. He has also not lost a Wimbledon match to a player ranked outside of the Top 10 since 2013, and has lost a mere 13 times in 21 career appearances at the event.

While Federer’s 2021 statistics have declined across the board from his career averages, he still carries a significant experience advantage over Hurkacz in the amount of grass court tennis he’s played in his career. His skill set and aggressive mentality will forever be amplified and rewarded by the quick, low bouncing courts at Wimbledon, and he has seen his serve broken just five times during the event. Additionally, while his numbers may be down by his standards, Federer still ranks 8th overall on the ATP Tour in Hold % (86.5%), and has held serve at an elite rate throughout his first four matches in London.

Since returning to the tour in March, eight of the twelve matches Federer has played have seen both he and his opponent capture at least one set. Given Hurkacz’s ability to keep pace with Federer on serve, Federer’s continued ability to execute his serve at an elite level, plus Federer’s seeming insistence on playing close matches since his return, a couple of narrowly-decided sets feel inevitable in this match.

To both hedge our upset pick and bet on the match to be tightly contested, let’s throw a unit on Federer/Hurkacz to go over 3.5 sets tomorrow. At worst, we lose half a unit, but get to celebrate 39 year-old Roger Federer’s attempt to make some history. At best, we double up our profits from this match and position ourselves extraordinarily well for the tournament’s home stretch

Moneyline Parlay – Matteo Berrettini (-360 over Felix Auger Aliassime) + Denis Shapovalov (-275 over Karen Khachanov): -134, 1.00 units to win 0.75

The case for Berrettini: Everything that FAA does well (big first serve, heavy/powerful forehand, willingness to move to the net), Berrettini does better.

FAA ranks 5th in Tennis Abstract’s grass-court specific Elo-Ratings. Berrettini ranks 4th. FAA made an ATP final on grass courts in the lead up to the 2021 Wimbledon. Berrettini won an ATP title. FAA ranks 17th in Hold % amongst Top 50 players. Berrettini ranks 3rd.

FAA will undoubtedly have some success holding serve against Berrettini (who’s backhand return remains his biggest liability), and can absolutely win a set in this quarterfinal matchup. He’s coming off of the biggest win of his career, and carries an 18-5 overall record in pro-level matches on grass courts. He’s chock full of confidence, and will be playing with house money the rest of the way.

That said, Berrettini is currently riding a 10-match win streak, is 25-6 in grass court matches for his career, joins Novak Djokovic as the only two men to make the Quarterfinal round at all three majors this season, looks like a middle linebacker on court, and is averaging career-highs in just about every advanced statistic across the board.

FAA is ready to compete for second weeks at majors. Berrettini is ready to compete for titles. The set scores will be close, but give me the Italian to advance to the semis.

Parlay Berrettini’s moneyline with Denis Shapovalov’s, who enters his Quarterfinal battle with Karen Khachanov as the more dynamic and significantly better rested of the two players , and the -134 odds become just intriguing enough to pull the trigger on a 1.00 unit wager.

Over 3.5 sets in Hurkacz/Federer + Over 3.5 sets in Berrettini/FAA + Over 3.5 sets in Khachanov/Shapovalov: +307, 0.50 units to win 1.53

This pick is essentially an amalgamation of all of the thoughts I’ve expressed in today’s piece.

It’s a Quarterfinal Wednesday at Wimbledon!! Whenever eight of the game’s best players go head-to-head with immense pressure on the line, things are bound to get funky!!

In fact, dating back to the 2016 Wimbledon, 11 of the 16 (.688) Men’s Quarterfinal matches have gone four sets or further. While I think Djokovic cruises with ease, I expect the other three battles to be absolute slugfests. With the margins between these players so thin, and the pressures of the event rising, let’s throw half a unit on three of tomorrow’s four Quarterfinal matches to go more than three sets, then kick our feet up and enjoy the ensuing chaos that unfolds.

To hear more about the logic behind these picks, tune into the daily Cracked Racquets Great Shot Podcast: Ace of the Day segment, a series singularly focused on negotiating the many wagering opportunities happening every day in the sport. If you’re interested in hearing recaps of each day’s results, or feel inspired to start following tennis more closely, tune into our Cracked Racquets “The Mini-Break Podcast” wherever you listen to your podcasts, or follow @crackedracquets on Facebook, Instagram, Twitter and YouTube.

Alex Gruskin is the Editor-In-Chief of Cracked Racquets, host of the Cracked Interviews Podcast/Mini-Break Podcast, and host of the “Ace of the Day” segment on the Great Shot Podcast – a Tennis Channel Podcast – which breaks down daily tennis prop bets, picks and parlays.

Written by OutKick Bets

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