World No. 1 Naomi Osaka made a major announcement last week, trumpeting her arrival as the latest tennis player to sign up with the mega-brand Nike and leaving her longtime apparel sponsor Adidas behind.

She’s not the first athlete Nike has swooped up after they’ve made a name for themselves on the global stage. While Roger Federer, Rafael Nadal, Victoria Azarenka and Maria Sharapova have worn the brand from the start, other all-time greats and future stars were a little late to the party.

Here’s a look at five of Nike’s biggest signings.

1

Serena Williams

Williams broke into the game and won her first major wearing Puma, but Nike soon swept in and their partnership has been game-changing: From denim to catsuits, tutus to “superhero” outfits, her attire has inspired many a think piece. Beyond the court, empowerment for women has been a major part of the relationship.

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2

Pete Sampras

Venerable brand Sergio Tacchini outfitted the young American at the start of his career, as he won his first four majors. In 1994, Sampras made his debut in Nike, winning Wimbledon in his soon-to-be-classic ensemble. He’d go on to break the men’s Slam singles title record wearing the brand, winning Wimbledon in 2000 for his 13th victory and then the US Open for his final Slam in 2002.

3

Simona Halep

After her longtime partnership with Adidas ended, Halep entered 2018 without a clothing sponsor. Proving that clothes do not make the player, she won her first tournament of the year in Shenzhen, then reached the Australian Open final. Nike entered the scene soon after that, and was there in time for her first Grand Slam title at the French Open.

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4

Sloane Stephens

In that French Open championship match, Halep faced Stephens, who had gotten on board with Nike going into 2018 after being one of the most prominent athletes to wear Under Armour. Stephens’ surprise title-winning triumph at the US Open in 2017 brought her further into the spotlight, and she further justified her place there with a win at last year’s Miami Open.

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5

Jim Courier

After reaching the finals of four of the eight prior Grand Slams—winning three of them—and reaching the top spot in the rankings. Courier started his 1993 season wearing Nike. Having been outfitted in Diadora to that point, the American would go on to defend his Australian Open title and reach two more major finals that year.

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