Daniil Medvedev probably thought nothing could hurt more than when he gave up a two-set lead in the 2022 Australian Open final to fall to Rafael Nadal.
This one might.
Without 10-time winner Novak Djokovic, Nadal or Roger Federer playing in the Open decider for the first time since 2005, the Russian surely thought it was his time to shed the tag of one-major wonder in his sixth grand slam final.
The world No.3 looked on track for a one-sided win at Melbourne Park on Sunday night, playing young Italian Jannik Sinner, in his first major final, off the court early on.
Medvedev broke the Italian in the fourth game and wrapped up the opening set in near-flawless fashion in just 36 minutes, before another 6-3 scoreline in the second.
But in a repeat of the epic five-set Nadal final when he took the opening two sets and had a triple break point for a 4-2 lead in the third, Medvedev faded, and so did his dreams of a second grand slam title.
He eventually succumbed 3-6 3-6 6-4 6-4 6-3, leaving the 2021 US Open trophy as the 27-year-old's lone grand slam triumph.
Medvedev had twice previously lost the decider at Melbourne Park, with a straight-sets defeat in 2021 to Djokovic and then heartbreak in five hours against Nadal a year later.
That demoralising defeat took him more than a year to recover from. Medvedev failed to make a final in his next six events and was unable to get past the fourth round at another major until Wimbledon in 2023.
He made a third-round exit at the Australian Open last year, with his ranking dropping from No.1 to outside the top 10.
Medvedev admitted he couldn't match the physicality of Nadal in 2022 and in this Open, the record 24 hours and 17 minutes he spent on court eventually proved telling against Sinner.
How he responds to his latest crushing defeat is anyone's guess - including Medvedev's.
"I felt really bad after Rafa's loss. I don't know how I'm going to feel in one week or in one month," the vanquished runner-up said.
"Sometimes the deception comes after, and, like, after Rafa's loss, was it the reason or not, I had my worst season?
"I don't know what's happening next, but I'm really going to try to keep the mentality that I go for next grand slam, and I go try to win there and in the middle there is going to be some other tournaments.
"If I play them, I play them to win. Otherwise I would stay at home with my family."
Had he prevailed, Medvedev would have set a new record for time spent in winning a grand slam, eclipsing the 23 hours and 40 minutes it took Carlos Alcaraz to take the 2022 US Open. As it was, he set the new time benchmark in a losing cause.
"At least I got a record in something. I'm in the history books for something. Let's take it," he said of the silver lining.
"It always hurts to lose in the final but probably being in the final is better than losing before.
"I always want to win but I guess I have to try harder next time but I'm proud of myself."
