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Caroline Wozniacki’s red-clay comeback ended abruptly at the 2024 Mutua Madrid Open, where she stumbled to a 3-6, 7-5, 7-5 defeat against Sara Errani in her first tour-level European red clay match since coming out of retirement.

Wozniacki, who originally hung up her racquets in 2020 to start a family, returned to action last summer with the Summer Olympic Games—which will take place on clay at Stade Roland Garros—firmly in her sights. But a medal on one of her least favorite surfaces may prove some doing for the Dane, who squandered a one-set lead to the former world No. 5—whom she'd led 4-1 in their head-to-head—and bowed out of Manolo Santana Stadium after two hours and 48 minutes.

Like fellow former No. 1 and tour mom Naomi Osaka, Wozniacki has played her best tennis on hard courts, winning the 2017 WTA Finals followed by the 2018 Australian Open in addition to a pair of runner-up finishes at the US Open. In her last season before retiring for the first time, she went winless on European red clay after reaching the finals of Charleston, which is played on Har-Tru.

Still, the 33-year-old has enjoyed success at the Caja Magica, reaching the final of the inaugural event in 2009 and the quarterfinals in 2015. The Dane looked in search of a similar run up against Errani, a former Roland Garros runner-up but currently ranked No. 100, and one who had to play two rounds of qualifying just to make it into the main draw.

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After an impressive run at the US Open, where she knocked out Petra Kvitova and pushed eventual champion Coco Gauff to three sets, Wozniacki’s biggest issue in 2024 has been closing matches: half of her losses this season have come after winning the first set, including at the Australian Open and Miami Open.

The same proved true against Errani, a blast-from-the-past rival she last played in 2018, on Wednesday. After easing through the first set and a myriad of service breaks, the second set saw both women push for ostensibly decisive service breaks, most crucially in the eighth game when Wozniacki held a break point that would have seen her serving for the match.

Instead, Errani turned the tables on Wozniacki, taking a 0-40 lead in the next game to score the first break of the set, and though she failed to serve out the set on her first opportunity, she made no mistake two games later to level the match at one set apiece.

Errani carried that momentum into the decider with an early 2-0 advantage but lost her nerve serving for 5-3 and Wozniacki edged back in to even the set at four games all.

Despite losing her lead, Errani kept pressure on return as she did in the second set and created two opportunities to serve for the match. Attempting an underarm serve on her first match point, Errani ultimately outrallied Wozniacki on the second to clinch the comeback in just under three hours.

Up next for Errani is a second-round meeting with No. 11 seed Beatriz Haddad Maia.