The Five Most Heart-Wrenching Tennis Breakups

By Anusha Rasalingam

Waking up today to learn that everyone’s favorite tennis couple, Wozzilroy, has called it quits was shocking. Particularly in today’s 24/7 media age, it’s not hard to get personally invested in the love lives of our favorite tennis stars – and these are the breakups that have hurt us, as fans, the most.

5. Lleyton Hewitt/Kim Clijsters

While they were together, many were surprised that Kim, known for her sweet, easygoing nature, and fiery, often confrontational Lleyton worked as a couple. In retrospect, it probably wasn’t surprising that the teenage lovebirds didn’t make it over the long haul. From two separate continents and with two seemingly opposite temperaments, popular Kim and polarizing Lleyton were together for five years, but broke up soon after becoming engaged.  Now, both are married with families of their own and have become respected legends of the game – so there was a happy ending, after all.

4. Radek Stepanek/Martina Hingis/Nicole Vaidisova/Petra Kvitova

Is there a word like modelizer in Czech for someone who only dates tennis players? Admittedly, without reading the Czech tabloids, it’s hard to get the scoop on what happened with Radek and his WTA love matches. With Hingis and Vaidisova, dating Stepanek coincided with the diminishing of their tennis careers – let’s hope Petra continues her strong, post-Radek form and breaks the curse. But, one thing’s clear, Radek knows how to charm the ladies of the WTA – at least for a time.

3. Serena Williams/Grigor Dimitrov

Another one that’s hard to take the pulse of.  Here’s what we know: Serena may have dated Grigor, and both were at the Mouratoglou Academy in Paris.  Fast forward, and Serena’s rumored to be dating Mouratoglou, and Grigor is caught canoodling with Maria Sharapova in Madrid during the clay court season. If this were the end of it, there wouldn’t be much to say – but Serena’s mysterious description of an unnamed female tennis player and a guy with a “black heart” in Rolling Stone led to this uncharacteristically personal attack from Sharapova during the pre-Wimbledon press:

2. Chris Evert/Jimmy Connors

While, for many of us, the lovebird Wimbledon is something we were too young to have witnessed, the image of the engaged Chrissie and Jimmy with their 1974 Wimbledon trophies is the epitome of storybook tennis romance. However, the demands of two top tennis careers, and, perhaps, divergent personalities led to a breakup of the engaged American sweethearts. For many years, the image of the two with their Wimbledon trophies is what endured from that time.  Unfortunately, Connors’ 2013 autobiography rehashed the decades-old breakup, detailing infidelities, and strongly hinted that Evert had an abortion. While often it’s hard to pick a side in a breakup, this one’s easy — Team Chrissie.

1. Rory McIlroy/Caroline Wozniacki

Maybe it’s the recency bias because this one is so new, but the only non-tennis player/tennis player pairing on this list is the one whose end seems the saddest. As a couple, Rory and Caroline both seemed to relish their domestic bliss – sharing so much of their lives, and their evident happiness, on Twitter.

Hardly ones to keep their happiness under wraps, we often saw them at each other’s tournaments, training together, and recently Rory employed a certain pink-haired caddy at Augusta. Because they let the world in on their unending stream of cheer and affection, their breakup seems even more tragic. I’m sure that, in time, we’ll all have more perspective, but until then, we still have Flabio!

2 Responses

  1. RZ
    RZ May 22, 2014 at 11:29 am |

    I seem to be the only person who doubts that Serena was referring to Dmitrov when she talked of the guy with the “black heart.” She had followed that statement with the lady in question never being invited “to the cool parties.” I’m pretty sure that Sharapova is invited to all of the cool parties…

  2. MisterMJ
    MisterMJ May 22, 2014 at 5:04 pm |

    Yeah, but you missed the teeny tiny detail that Rory is a pro golfer. How about Verdasco-Ivanovic … two of the (arguably) better looking players on tour. I guess Ana felt she was always fighting Fernando for bathroom mirror time in the mornings.

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