The Ladies Tennis Masters, as its name suggests, is intended for former top players who have retired from top-level professional competition.

On Thursday, Kontaveit, 29, who won the event in 2023, conceded just one game in the opening set to Medina Garrigues, 43, and took a 4–1 lead in the second, though the Spaniard showed some fighting spirit and closed the gap to within one game.

The Estonian, however, finished confidently, sealing a victory to secure a place in the semifinals, where she will face Alizé Cornet (France).

"I'm quite surprised — I was feeling the ball well, found my shots, and played some really good tennis. I didn't know what to expect, but I'm happy. It felt really good out there, I won't lie," Kontaveit said after the match. "I felt like I used to — I really enjoyed playing. I haven't felt that in a while. I'm grateful that we're given this kind of opportunity with this tournament," the former world number two said post-match.

Cornet got a walkover win in round one against former world number one and Wimbledon and French Open champ (both in 2003) Kim Clijsters of Belgium, who had to retire due to an ankle injury picked up in the second set.

Two more quarterfinals remain to be played on Friday, with Angelique Kerber (Germany) facing defending champion Kirsten Flipkens (Belgium) and Eugenie Bouchard (Canada) playing Barbora Strycova (Czech Republic).

The semifinals take place on Saturday; the final is on Sunday.

Kontaveit was world number two as recently as June 2022, but this was also the year that chronic lumbar pain and other injuries started to dog her, ultimately prompting her retirement the following year. Her final top-level event was Wimbledon 2023, though she took to the court both for the Masters that year and in an exhibition game at home in Tallinn versus Ons Jabeur.

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