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Brad Gilbert claims Serena Williams has been practicing with the son of a tennis legend ahead of Wimbledon

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With Wimbledon just days away from getting underway, there is, unsurprisingly, still one story that is dominating the headlines.

After all, 12 months ago it seemed wholly unfathomable that we would ever see Serena Williams back on the tennis court in any capacity, let alone to play singles at Wimbledon.

The sporting world will certainly standstill when she does return, with tomorrow’s draw particularly intriguing given that, because she is a wildcard, the 23-time Grand Slam champion could be drawn against anyone.

The main question surrounding Serena is how she might look on the singles court, having only had the opportunity to play two doubles matches thus far in her comeback.

Well, Brad Gilbert has some insight to offer, having spoken to Darren Cahill, who has been watching her train at Wimbledon.

Brad Gilbert reveals what Darren Cahill has told him about Serena Williams

Speaking on the Big T podcast, he began by outlining his surprise at Williams’ decision to play singles at all.

The legendary coach admitted: “First of all, you know, I’ve been saying for a while. I thought for sure she was just gonna play doubles, and if she did [play singles], it would maybe be this summer like, at a Washington or Cincy. So I’m surprised.

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“It’s just like she’s starting off in a major!”

He then provided his unique insight: “I do have some intel. The last couple of days, she’s been practising at Aorangi, and Darren Cahill told me that she’s been playing the same time as Sinner.

“He said he watched her the last couple of days. I mean, she’s been grinding two and a half hours on the court. She was hitting with young Cruz Hewitt.

Serena Williams enters the Wimbledon grounds in 2026.
Photo by Matthew Stockman/Getty Images

“He said, she’s playing very good, looks a lot more sure of herself and confident playing singles.

“What’s tricky is in doubles, sometimes, even though it’s less movement, you’re not always in control of what’s happening, you know, because you’ve got a partner, it’s stagnant at times. He said she looked a lot more comfortable and was hitting the ball big and working a lot on first-strike tennis.”

This comes not long after Kim Clijsters stated what she’ll be looking out for when Serena plays singles.

Danielle Collins predicts how far Serena Williams will go at Wimbledon

Following on from Gilbert’s prediction, Danielle Collins was then asked to offer her opinion on how far Williams might be able to go at Wimbledon despite her lack of practice.

She insisted: “Yeah, look, I mean, I do think Serena is the GOAT. Serena’s capable of anything, I think even with time off, I think she could beat any player on any given day.

“At the same time, I do think it’s a little bit draw dependent, right? It could be interesting. She could go against, you know, a qualifier first round, or she could play Sabalenka, and that could be, you know, maybe a little bit trickier.

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“Anything can happen on the women’s side, so it’s so hard to say, especially not having seen Serena play any singles matches leading up to this.”

Collins had been impressed with her performances on the doubles court at least, adding: “I will say, I thought she looked good in the doubles, and I’m really excited to see her take the court with Venus. Venus played a great match today.

“But, yeah, it’s really just tough for me to make a prediction on that, and I typically tend to say that Serena was one of my favourite players growing up, so I really believe that she can be anybody, even having so many years off.”