Federer and 15 others: Who has the best chance of a Wimbledon upset?

Roger Federer remains an overwhelming favorite to win Wimbledon after storming through his first three matches without getting broken a single time. In fact, he has not even been pushed to deuce during any service game. The 36-year-old Swiss is less than even money to capture the title, but does that mean his ninth triumph at the All-England Club is a foregone conclusion? Heading into the second week, 15 other players are still alive and in contention to be the one who knocks out Federer.

Here they are from No. 15 down to No. 1–not in terms of their chances to win the whole thing, but their chances in a hypothetical head-to-head showdown against Federer.

15. Mackenzie McDonald – McDonald had won only three ATP-level matches prior to this fortnight. The 23-year-old has made a great run, but he benefited from Marin Cilic’s exit and has not done anything to suggest he can challenge Federer. And he probably won’t get the chance, because he would have to upset Milos Raonic and then either John Isner or Stefanos Tsitsipas.

14. Gilles Simon – Simon stunned Federer twice in 2008 but now trails the head-to-head series 6-2 after once leading it 2-0. It may seem like 2008 is walkin’ through that door again with Simon in the second week of a slam and the top of the rankings featuring Rafael Nadal and Federer, but it wouldn’t walk through that door again if it’s Fed-Simon in the final.

13. Jiri Vesely – Time is still on Vesely’s side at 24 years old, but for now he is a talented underachiever who has never been ranked higher than 34th in the world. He does, however, have to be taken seriously at Wimbledon; he is 10-4 overall and this is his second trip to the second week. But the Czech is 2-15 lifetime against top 10 opponents (with one win coming against Dominic Thiem on grass).

13. Gael Monfils – Monfils is a respectable 4-9 lifetime against Federer, but two of the wins came on clay and another was during the Swiss’ disaster year in 2012. The Frenchman has squandered plenty of other opportunities in this matchup (including four times at the French Open), and those were when he was in better form than he is now.

11. Stefanos Tsitsipas – Tsitsipas has plenty of talent to compete with the best players in the world, but he is just 19 years old and a meeting with Federer in the Wimbledon semifinals could be an overwhelming occasion. The Greek had never won a main-draw match on grass prior to this season.

10. Adrian Mannarino – Mannarino is somewhat like Simon to 2.0; not as good as Simon in his prime, but certainly a younger, better version at the moment. He isn’t necessarily going to beat you, but he isn’t going to beat himself. You have to play well to get the best of him; and you have to play great to get the best of him on grass. Unfortunately for Mannarino, Federer is playing great–and is dominating the head-to-head series 5-0 (12-1 in total sets).

9. Karen Khachanov – Starting with Khachanov, the next nine players on this list all boast considerable firepower with at least one shot (and in some cases many shots) and can thus seriously trouble Federer at times. The 22-year-old Russian, however, is 0-7 lifetime against former Grand Slam champions. A final against the eight-time Wimbledon champion would be as tough as it gets.

8. Kei Nishikori – Nishikori takes time away from opponents by playing on top of the baseline and striking his two-handed backhand better than almost everyone. His style worked to perfection against Nick Kyrgios–again–in the Wimbledon third round. On his worst surface, though, the Japanese world No. 28 would have to play the match of his life.

6. Kevin Anderson – Anderson is 1-14 lifetime against Federer, Nadal, and Novak Djokovic, 0-9 against Federer and Nadal, and 0-4 against Federer. Needless to say, his chances in the quarterfinals would not be good. But he has a bigger serve and plays bigger from the baseline (aside from Nishikori’s backhand) than the aforementioned contenders. Anderson has also enjoyed plenty of success at WImbledon and he is a former slam finalist (2017 U.S. Open).

6. Ernests Gulbis – Gulbis would have a couple things going for him in a contest with Federer. He fears no one, possesses a huge serve and backhand, and has upset Federer at a Grand Slam once before (in five sets in the 2014 French Open fourth round). As the Latvian showed against Alexander Zverev on Saturday, his best can still beat basically anyone. He’s just very rarely at his best.

5. John Isner – Like Federer, Isner has not been broken through three rounds. These grass-court conditions are suiting Isner better than normal, as the ball is flying through the air in relatively hot, dry weather and also bouncing high. Even against Federer, almost any Isner match can be a 50-50 proposition when he serves well. It wouldn’t be 50-50 against Federer in the Wimbledon semis, but it would certainly be a scary one for the Swiss.

4. Milos Raonic – Raonic is always a question mark from a physical standpoint, but if he can get past McDonald in swift fashion and then beat Isner or Tsitsipas with his body fully intact, those questions would lessen. The Canadian has defeated Federer on three occasions, including in the 2016 Wimbledon semifinals. This is a much different Federer now, of course, but Raonic will believe in himself against anyone on this surface.

3. Juan Martin Del Potro – This is one of the best rivalries in tennis. The 18-7 margin in Federer’s favor is relatively competitive by Federer standards, and it is even more so than that number suggests. Instant classics between them are too many to name here. Grass is not Del Potro’s best surface so he would be a considerable underdog, but the Argentine has been clobbering people to far this fortnight.

2. Novak Djokovic – Djokovic is 2-1 against Federer on grass, including 2-0 in Wimbledon finals (the stage at which they would meet this time around). The former world No. 1’s comeback is gaining steam and although the jury is still out on just how well he is playing, he would likely have to get past either Nadal or Del Potro in the semis before facing Federer. If Djokovic does that, watch out in the title match.

1. Rafael Nadal – Conditions at Wimbledon always suit Federer, and so far this fortnight they are treating Nadal just fine. Both all-time greats were dominant in week one, so a rematch of the epic 2008 final 10 years later is not only looking like a real possibility but is also shaping up to be another classic if it happens. Despite having lost five in a row, the Spaniard still leads the head-to-head series 23-15.

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