We are into the fourth round at Wimbledon, the third Grand Slam tennis event of the year and the only major championship played on grass. Here’s a look at Monday matches involving the two tournament favorites on the men’s side, top-seeded Novak Djokovic and No. 2 Roger Federer, along with the latest Wimbledon odds.
2019 Wimbledon Odds, Preview & Picks for Men’s Round of 16
No. 1 Novak Djokovic vs. Ugo Humbert
- 2019 Wimbledon Odds: Djokovic -9999 / Humbert +1115
To reach the fourth round, Humbert knocked off Auger-Aliassime 6-4, 7-5, 6-3 in two hours and nine minutes last Friday. Humbert had never advanced past the second round of a Grand Slam. He is the 43rd man in the Open Era to make the Round of 16 at the grass-court major on his debut. In the first round, the lefty moved to 2-0 against Top 20 opposition when Gael Monfils retired down 0-3 in the fifth set in their battle, which Monfils led two sets to none.
Just a year ago, Humbert was ranked No. 290 and playing an ITF Pro Circuit event in France. Since then, he’s won four ATP Challenger Tour titles and finished runner-up in three others. This match will be his first-ever against a Top 10 opponent.
Djokovic, a four-time Wimbledon champion, beat 22-year-old Hubert Hurkacz to advance. The Serb won 7-5, 6-7(5), 6-1, 6-4 and returned to the Round of 16 at The Championships for the 12th time. Djokovic tied Boris Becker for third place in the Open Era for most Round of 16 appearances at Wimbledon, trailing only Jimmy Connors and Roger Federer (16).
For two sets, Hurkacz gave Djokovic all he could handle, but Djokovic took advantage of a lull in Hurkacz’s level to start the third and broke once in the fourth set as Hurkacz never retained the same level he brought in the opening two sets. Djokovic cruised to the finish line, winning over 60 percent of the total points in the final two sets.
This is the first-ever meeting between Humbert and Djokovic.
No. 2 Roger Federer vs. No. 17 Matteo Berrettini
- 2019 Wimbledon Odds: Federer-909 / Berrettini +503
Federer was pushed early in his third-round match and in danger of dropping the first set for the second time this tournament. But one 10-minute surge was all the 37-year-old Swiss needed to take control of the match move into the second week at The Championships for the 17th time.
Federer defeated Australian Open semifinalist Pouille 7-5, 6-2, 7-6(4), becoming the first player in history to earn 350 Grand Slam singles wins. He is also the first man in the Open Era to reach the fourth round at Wimbledon 17 times, breaking a tie with Jimmy Connors.

The biggest moment of the match came at 5-5 in the first set, when Pouille earned a breakpoint that, if converted, would have allowed him to serve for the opener. Federer used two overhead smashes to stave off that chance, and never looked back from there, winning the next six games to take a commanding lead. Federer appears on a collision course in the semifinals with rival Rafael Nadal, who also plays Monday. Nadal has not won the Wimbledon title since 2010.
Berrettini defeated No. 24 seed Diego Schwartzman in a five-set thriller. Federer has said that he doesn’t know Berrettini very well but added that it bodes well to see the newer, younger talents playing well on Tour.
“So that makes it a bit more tricky, as well. I saw him play a little bit in Halle. Saw his run, of course, in Stuttgart. Now he’s backing it up here again. That’s not easy to do, especially when you’re sort of newer on the Tour,” Federer said.
The Italian has been one of the surprise stories of the grass-court season, winning 11 of his 12 matches to date. Berrettini boasts wins over Nick Kyrgios, Felix Auger-Aliassime and Karen Khachanov (twice). Berrettini has gotten pointers from Craig O’Shannessy who also works as Novak Djokovic’s strategy analyst. The 23-year-old has climbed from outside the top-50 to inside the top-20 in the last three months and his rapid rise has coincided with the deployment of tactics expert O’Shannessy behind the scenes.
Berrettini is a tall guy and he possesses a huge serve. He blasted 22 aces against Schwartzman, 16 against Marcos Baghdatis and 19 against Ajlaz Bedene in the previous rounds. It’s the first ever-meeting between Berrettini and Federer.