Novak Djokovic has played over 1,000 matches in his career against a variety of players.
The Serbian legend has won 24 Grand Slams, defeating the likes of Rafael Nadal, Roger Federer, and Andy Murray in major finals.
He has also lost major finals to the three players listed above…
Djokovic lost multiple Grand Slam finals against just five players in his career: Nadal, Federer, Murray, Carlos Alcaraz, and one other tennis icon.
During an interview in the lead-up to the 2025 Hellenic Championship, Djokovic named that player as the most ‘underrated’ ATP star he faced during his entire tennis career.
Novak Djokovic says Stan Wawrinka is the most ‘underrated’ player he’s ever faced
One name immediately came to Djokovic’s mind when asked to pick the most underrated player he’d competed against.
“Most underrated player I ever faced, I mean [Stan] Wawrinka,” he said.
“I think he is very underappreciated and underrated, considering he is a three-time Grand Slam champion.
“I think people often forget about him and what he’s achieved.
“He’s achieved more than 90% of the players ever in the history of the game.”
Djokovic knows all too well how dangerous Wawrinka can be, having lost four of their nine Grand Slam meetings.
| Match | Winner | Loser | Score |
| 2023 Wimbledon – 3R | Novak Djokovic | Stan Wawrinka | 6-3, 6-1, 7-6 |
| 2019 US Open – 4R | Stan Wawrinka | Novak Djokovic | 6-4, 7-5, 2-1 (RET) |
| 2016 US Open – F | Stan Wawrinka | Novak Djokovic | 6-7, 6-4, 7-5, 6-3 |
| 2015 French Open – F | Stan Wawrinka | Novak Djokovic | 4-6, 6-4, 6-3, 6-4 |
| 2015 Australian Open – SF | Novak Djokovic | Stan Wawrinka | 7-6, 3-6, 6-4, 4-6, 6-0 |
| 2014 Australian Open – QF | Stan Wawrinka | Novak Djokovic | 2-6, 6-4, 6-2, 3-6, 9-7 |
| 2013 US Open – SF | Novak Djokovic | Stan Wawrinka | 2-6, 7-6, 3-6, 6-3, 6-4 |
| 2013 Australian Open – 4R | Novak Djokovic | Stan Wawrinka | 1-6, 7-5, 6-4, 6-7, 12-10 |
| 2012 US Open – 4R | Novak Djokovic | Stan Wawrinka | 6-4, 6-1, 3-1 (RET) |
Two of those matches were Grand Slam finals, as Djokovic came up short against Wawrinka at Roland Garros in 2015 and at the US Open the following year.
His 2015 French Open final defeat was particularly memorable, as Djokovic missed out on a golden opportunity to complete his Career Grand Slam.
When Djokovic beat the greatest clay-courter of all time, Nadal, in the quarterfinals, he looked destined to finally get his hands on the La Coupe des Mousquetaires trophy.
It wasn’t to be, however, as Djokovic was denied by the brilliant Swiss star, who collected the second of his three major titles in style.
Djokovic won his first French Open title in 2016, defeating Murray in the final, but would no doubt have loved to get the job done against Wawrinka a year earlier.
The pair haven’t played each other in over two years, but had a chance to meet this week in Athens.
Wawrinka got off to an excellent start in the Greek capital, but couldn’t quite get over the line in his second-round match.
Stan Wawrinka loses to Lorenzo Musetti in Athens thriller
Picking up his fourth tour-level win of the season, Wawrinka took down Botic van de Zandschulp, 2-6, 7-6, 7-5.
Advancing to the second round, Wawrinka met ATP Finals-chasing Lorenzo Musetti and made a fast start.
Looking to pick up his first top 10 win in over a year, Wawrinka won the opening set 6-4, as he edged closer to a rare quarterfinal appearance.
| Match | Opponent | Opponent’s rank | Score |
| 2024 Stockholm Open – QF | Andrey Rublev | 7 | 7-6, 7-6 |
| 2023 Cincinnati Open – 2R | Frances Tiafoe | 10 | 6-3, 6-4 |
| 2023 Indian Wells – 3R | Holger Rune | 8 | 6-2, 6-7, 7-5 |
| 2022 Swiss Indoors – 1R | Casper Ruud | 3 | 6-4, 6-4 |
| 2022 Moselle Open – 2R | Daniil Medvedev | 4 | 6-4, 6-7, 6-3 |
Coming just a few points away from victory, the 40-year-old lost out in a second-set tiebreaker, 6-7 [5-7], as Musetti kept his Turin hopes alive.
Pushing on in the decider, Musetti secured the win 4-6, 7-6, 6-4, booking his place in the quarterfinals, where he will meet Alexandre Muller.
Set to jump up to 155th in the world thanks to his efforts in Athens, Wawrinka will now rest up ahead of the 2026 ATP Tour season.
Only time will tell how much longer Wawrinka will compete for, but it certainly looks like he’s still got more left in the tank…
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