The American will face the victor of Serena Williams and Carina Witthoft, with their match getting underway at midnight (BST) tonight.
But 20 years since the sisters' first collision course in the Australian Open, which Venus won 7-6 (7-4), 6-1, another chapter awaits Friday.
"Friday will be incredibly hard", said Serena before jokingly hitting back at Venus's claim that when they last met at a Slam in the final of the 2017 Australian Open her sister had an advantage as it was "two against one".
Williams, a 23-time Grand Slam singles victor, said in May she wore the outfit to help her cope with blood clots.
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The 23-time Grand Slam victor wore compression fishnets with her tutu looks to guard against blood clots, a problem she battled soon after giving birth last September.
"I hope that we get to play. That's why I'm very lucky to play in the same time as they are".
In response Williams dominated her first match in the US Open against Poland's Magda Linette, wearing an asymmetrical Virgil Abloh x Nike tutu paired with sparkly silver sneakers from the same "Queen" collection and compression fishnet tights - to tackle the blood clots in style. "It's a tough draw".
And today, in her second win - this time against Germany's Carina Witthöft she wore the same outfit only this time it was in lavender.
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"It has been wonderful to play out here on Louis Armstrong Stadium". I was inspired by that, and I was like, 'We need to make a comfortable denim pant that doesn't have a ton of stretch in it.
"Definitely I'm going to watch this match". That love-40 game at 4-4 was not looking good.
"Everybody was pretty scared that I could get a fine for it", added the world number 31.
"You have to play who you have to play".
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