Adding salt to the raw wound, Thanasi Kokkinakis' gut-wrenching second-round Australian Open loss will leave the in-form star scrambling to make the main draw of the season's remaining three grand slam events.
As if he was not already crushed enough after letting a two-sets-to-love and 5-2 lead slip against Andy Murray, Kokkinakis is now in a desperate race against the clock to lift his flagging ranking before the French Open in May.
Despite finally being free of injury and playing the best tennis of his career, Kokkinakis is projected to be languishing at No.135 in the world after the Open.
The 26-year-old needs to climb back into the top 100 to be guaranteed direct entry to Roland Garros, where he once reached the third round as an exciting teenage talent and shared centre court with Novak Djokovic.
If he cannot, the South Australian will need to try his luck in qualifying, or rely on Tennis Australia awarding him the only wildcard they are issued under a reciprocal arrangement with the French Tennis Federation.
The rough predicament is a cruel postscript to the most dispiriting defeat of Kokkinakis luckless, injury-plagued career.
The one-time Roger Federer slayer was already reeling physically and mentally from the five-hour, 45-minute heartbreaker that finished at 4.05 on Friday morning.
"Don't really know what to say .... Wow, this f***ing sport man," Kokkinakis posted on Instagram while trying to digest the 4-6 6-7 (4-7) 7-6 (7-5) 6-3 7-5 defeat.
"Gave it everything I had last night and fell short. You're a warrior @andymurray and a honour to share that court with you.
"To everyone that supports me, THANKYOU."
Kokkinakis' bitter pill ends his 2023 Open campaign after he was forced to withdraw from his doubles title defence when playing partner Nick Kyrgios pulled out of the singles on Monday with a knee injury.
His departure leaves 22nd seed Alex de Minaur and fellow Sydneysider Alexei Popyrin to fly the Australian flag in the singles.
De Minaur plays Frenchman Benjamin Bonzi on Saturday for a place in the last 16, with Popyrin up against American Ben Shelton as the wildcard chases a spot in the second week of a grand slam for the first time.