On a day when all four Australian women crashed out in the clay-court event, Kasatkina suffered the most frustrating reverse, succumbing 6-3 3-6 7-6 (15-13) to qualifier and lucky loser Daria Snigur after being unable to convert four match points.
Twelve months on since transferring her allegiance to Australian tennis amid much fanfare, the 28-year-old Russian-born star has found it difficult to maintain her best form amid a turbulent time in her life, and even walked away from the sport at the end of last year admitting she was at "breaking point".
Now after suffering another hip injury that took two months out of her 2026 season, Kasatkina has returned to the court with two more defeats -- and none more painful than Wednesday's defeat to Ukrainian Snigur as she lost the longest regular third-set tiebreak in WTA events for eight years.
Going down 6-3 3-6 7-6 (15-13) in the two-hour 23-minute battle, it must have been a hard one to take for Kasatkina, who had four match points repelled and also saved six of her own before hooking a forehand wide.
The defeat left her with a record of four wins and eight losses for the season, and having played her first match as an Australian last April when No.12 in the world and No.1 in the country, Kasatkina will now plummet to Australian No.5 and at least world No.83 in the next rankings -- her lowest since 2015.
She still must be trying to fathom how she lost this remarkable, entertaining match, having served for it at 6-5 in the final set when she earned her first match point.
But world No.98 Snigur, a lucky loser playing her first career tour-level match on clay, proved inspired in thwarting her more experienced opponent, leaving the Aussie looking astonished when she pulled off one incredible backhand pass at full stretch when match-point down at 7-6 in the breaker.
Kasatkina wasn't the only Australian luminary to tumble at the famed Caja Magica venue, with the country's No.2 Talia Gibson, breakthrough star of the hard-court swing in the US, finding the clay much more of a slog as she went down 6-3 6-2 to Colombian Emiliana Arango.
World No.85 Ajla Tomljanovic lost to Hungary's 117th-ranked 7-6 (9-7) 6-4, while Kim Birrell also succumbed to Hungarian opposition in the shape of world No.78 Panna Udvardy 4-6 1-6 6-1.
It's now down to the Australian men in Madrid with Alex de Minaur, Alexei Popyrin and Adam Walton all ready for action in the main draw.
