Bianca Andreescu and Naomi Osaka clashed on the tennis court for the first time in five years and the two former Slam champs didn’t disappoint, but it was Andreescu who ultimately got the better of Osaka, 6-4, 3-6, 7-6 (3) to reach the Libema Open semifinals.

Andreescu was playing only her second tournament of 2024 after missing the last nine months due to a back injury, but navigated a high-quality clash with a resurgent Osaka to outlast the former world No. 1 in two hours and 15 minutes on Center Court.

Improbably, Andreescu and Osaka were facing off for the first time since 2019, when the two played one of the best matches of that season at the China Open. At the time, Andreescu had just won her first Grand Slam title at the US Open, was riding a 16-match hard-court win streak, and had never lost a match to a Top 10 player. Osaka was also in the midst of a career-best season, having kicked off the year with a first Australian Open victory and rise to world No. 1.

In the five years since that three-set stunner, both have endured numerous physical and emotional hurdles: Osaka took the 2023 season off to give birth to her first child while Andreescu has only managed a part-time schedule due to various injuries. A stress fracture to her back kept the Canadian off-court from August to May, when she enjoyed a successful comeback at Roland Garros.

Osaka had also enjoyed a revelatory result in Paris, pushing world No. 1 Iga Swiatek to within a point of defeat in the second round and seemingly putting her natural surface demons to rest despite ultimately losing to the eventual champion in three sets. Making another seamless surface transition, the four-time major champion won back-to-back matches on grass for the first time since 2018, defeating No. 4 seed Elise Mertens and Suzane Lamens to book the rematch with Andreescu, a fellow wild card who scored an upset over No. 6 seed Yuan Yue.

A runner-up in Bad Homburg back in 2022, Andreescu has shown potential on grass in years past and channeled that into a high-quality first set against Osaka. Despite numerous rain interruptions, the 23-year-old scored the lone break off a stunning volley to serve it out after 40 minutes.

Osaka roared back in the second, taking a 5-0 lead and withstanding a late surge from Andreescu to force a decider with a big serve out wide.

Both women saved break points as the third set got underway but it was Andreescu who broke first, landing a backhand return winner en route to a 4-2 lead and putting down a strong serve to put herself within a game of victory.

Osaka delivered an incredible reply, holding serve to stay in the match and opening the ninth game with a powerful forehand winner. Serving for the match, Andreescu dug out of a 0-30 deficit with a pair of aces but Osaka kept pressing, striking another forehand winner and breaking serve off a backhand miss and holding again to level the contest.

Andreescu stopped the run of games against her to edge back into the lead but Osaka put down a hold at love to send the match into a deciding tiebreaker. The excitement continued in the Sudden Death as the two exchanged mini-breaks through the first change of ends, with Andreescu stumbling but keeping things even at three points apiece.

Serving with a 4-3 lead, Andreescu was first to match points thanks to a wicked forehand slice, narrowly converting when an Osaka forehand clipped the netcord and dropped back onto her side.

Awaiting Andreescu in the semis is Hungarian qualifier Dalma Galfi.