Caroline Wozniacki and Serena Williams played 11 matches against each other on the WTA Tour.
Meeting for the first time in 2009, Williams fought back from a set down to defeat the Dane, 6-7, 6-3, 7-6 in Sydney, Australia.
Williams continued to pick up wins over Wozniacki until the 2012 Miami Open, where she fell to a straight-set defeat.

Unfortunately for Wozniacki, that was the last time she beat Williams, as their WTA Tour head-to-head record stood at 10-1 in the American’s favor when she retired from tennis.
Speaking today, Wozniacki has shared why she struggled as much as she did against the 23-time Grand Slam champion.
Caroline Wozniacki says Serena Williams could ‘do anything’ which really frustrated her
Appearing as a guest on the ‘Nothing Major’ podcast, Wozniacki commented on her one-sided rivalry with Williams.
“I think Serena [Williams] is the toughest opponent I ever had to play. Growing up, I would see Serena and Venus [Williams] on TV, and I remember thinking I don’t know how I am going to figure out a way to beat them, but eventually I am going to have to, or maybe they grow old and don’t move as well,” she said.
“That just didn’t really happen. So Serena, the fact that she could serve and have the same ball toss for every serve. She could take pace off, she could hit 220kmph down the middle, she could do anything.
| Match | Winner | Loser | Score |
| 2014 WTA Finals – SF | Serena Williams | Caroline Wozniacki | 2-6, 6-3, 7-6 |
| 2014 US Open – F | Serena Williams | Caroline Wozniacki | 6-3, 6-3 |
| 2014 Cincinnati Open – SF | Serena Williams | Caroline Wozniacki | 2-6, 6-2, 6-4 |
| 2014 Canadian Open – QF | Serena Williams | Caroline Wozniacki | 4-6, 7-5, 7-5 |
| 2013 China Open – QF | Serena Williams | Caroline Wozniacki | 6-1, 6-4 |
| 2012 Olympics – QF | Serena Williams | Caroline Wozniacki | 6-0, 6-3 |
| 2012 Madrid Open – 3R | Serena Williams | Caroline Wozniacki | 1-6, 6-3, 6-2 |
| 2012 Miami Open – QF | Caroline Wozniacki | Serena Williams | 6-4, 6-4 |
| 2011 US Open – SF | Serena Williams | Caroline Wozniacki | 6-2, 6-4 |
| 2009 WTA Finals – SF | Serena Williams | Caroline Wozniacki | 6-4, 0-1 (RET) |
| 2009 Sydney – QF | Serena Williams | Caroline Wozniacki | 6-7, 6-3, 7-6 |
“I think that was really frustrating, the fact that she had a lot of power but could still move. She was by far the best player I have ever played.
“I think she is the best player ever, obviously not talking about Novak [Djokovic].
“But I think just being such a full and complete player that she was, if you made her angry, it was just going to be worse for you, so you just try and stay in your lane and play every shot.

“I beat her once, and I lost many, many times.”
Wozniacki believes Williams had a big influence on an entire generation of WTA stars.
“I think she was a big reason for why our generation also had to really step up and try and get better every single practice session and every match,” she said.
“She was really there and really taking the throne of everything.”
Despite all her shortcomings against the American tennis legend, Wozniacki insists she still loves Williams.
‘We have a lot in common’ – Caroline Wozniacki on her relationship with ‘sister’ Serena Williams
Wozniacki didn’t have a bad word to say about Williams, as she explained how well the 44-year-old treated her when they were on tour together.
“I love Serena. She is the best,” said Wozniacki.
“Obviously, she is a Mom, and I am a Mom. We have a lot in common in that regard, obviously having been on Tour for so long.
“She was a way better tennis player than I was, but that’s okay! Nobody really has gotten to her level, so I’m okay with that.
“Just as a person, if I was struggling with something either personally or on the tennis court, she was always there to pick me up.

“If I was doing great, she was there to cheer me on and to have someone who goes through the same things in life as you, it really just felt incredible to feel like you have a sister on Tour.”
Wozniacki recalled how she was ‘welcomed’ into the Williams family back when she was just 17.
“Venus really took me under her wing on Tour and is probably the main reason why Serena and I became friends,” she said.
“When I was 17, I played an exhibition in Hong Kong, and I ended up being teamed with Venus in doubles. And after that, I think Venus was like this girl plays pretty well and asked me if I would play a doubles tournament with her in Doha.
“I did, and Serena was like Venus never plays with anyone else, who is this girl you are playing with?
“So she came up to me and we had a little conversation, and she was like I see it now, I get it. Welcome to the family!”
Williams and Wozniacki maintain a close relationship today, as their intense rivalry turned into a long-lasting friendship.
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