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50 Hottest Sports Flings Ever

Gabe ZaldivarPop Culture Lead WriterNovember 18, 2010

50 Hottest Sports Flings Ever

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    Tony Parker and Eva Longoria are splitting. It is sad news for fans of marriage. But I submit to you that their marriage lasted a lot longer than most relationships.

    Just look at Tony Romo. He gets a new girlfriend every time the Cowboys get another win. If the Cowboys play their cards right, that could be three Tony Romo girls on the season. Now wouldn't that be something. 

    I tell you, sports and sex are fickle things. One day you are madly in love and the next you are dropping your significant other like they were a torn batting glove.

    But Tony and Eva, they lasted for three years. In the life of an athlete, that's a lifetime. 

    We are looking for a few things here, folks. I an judging on looks and how hot the fling would have been.

    So, here are 50 flings to get you going into the weekend. 

50. Michael Phelps and Amanda Beard

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    Rumors were numerous that these two hooked up. Beard has denied the allegations and Phelps has remained mum. I'm going to go ahead and say they did. 

49. Gina Carano and Kit Cope

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    It looks like two martial arts experts can't figure out how to make things work. Who would have thought?

48. Michael Phelps and Maria Ho

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    Michael Phelps and Maria Ho hooked up back in October 2008. She is a poker player and he is a decent swimmer.

    Sure he can swim the 100 better than anyone, but can he find me in a game of Marco Polo? I think not. 

47. Shawne Merriman and Tila Tequila

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    This fling was so hot the pair almost killed each other. The two dated for a couple of months before Merriman allegedly tried to choke her.

    I'm guessing she was attempting to sing one of her songs at the time. 

46. Natalie Gulbis and Ben Roethlisberger

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    The hot LPGAer was once rumored to be dating Ben Roethlisberger. I imagine they hit a snag everytime an 18 year-old passed into view. 

45. Cristiano Ronaldo and Gemma Atkinson

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    Amidst the numerous women that Ronaldo has been with is the English TV personality Gemma Atkinson.

    It seems that women are into money, good looks and fame. I may have picked the wrong profession. 

43. Alicia Sacramone and Brady Quinn

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    Gymnast Alicia Sacramone is dating Browns quarterback Brady Quinn. One of these athletes boasts a skill that is useful in the bedroom.

    No, I'm not talking about a no-huddle offense. 

42. Cristiano Ronaldo and Nereida Gallardo

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    The aspiring model has been linked to not only Cristiano Ronaldo but fellow Real Madrid star and Spanish national team player Sergio Ramos. 

41. Michael Phelps and Stephanie Rice

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    Michael Phelps had a big summer in 2008. He got his mack on with fellow swimmer Stephanie Rice.

    Oh, and he won eight gold medals. If you care about such trivialities. 

40. Cristiano Ronaldo and Bipasha Basu

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    Ronaldo seems to be one of the most liked athletes on this list. He was seen making out with Bollywood actress Bipasha Basu some time ago.

    I have not seen her before now but I have to say, I'm a fan. 

39. Cristiano Ronaldo and Paris Hilton

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    The two were seen everywhere together in June 2009. He is a world-class athlete, who is one of the best in his respective sport. She is the daughter of a dude with a lot of money.

    Can't really see why they didn't get along better. 

38. Michael Phelps and Brittny Gastineau

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    This relationship is so new and secret that I am going to assume it burns out before it gets started.

    The two were seen all over Los Angeles earlier this week. 

37. David Beckham and Rebecca Loos

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    You can't be as handsome and successful as David Beckham and not welcome scandal. Beckham was rumored to have hooked up with the model Rebecca Loos in 2004. 

    Becks denied the allegations. But what else is a married man to do?

36. Cristiano Ronaldo and Kim Kardashian

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    Before she was getting all snuggly with Miles Austin, Kim was locking lips with Ronaldo in April 2010.

    She sure does like her athletes. More reason for me to put more of her in this list. Thanks, Kim. 

35. Iker Casillas and Ariadne Artiles

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    The Spanish goalkeeper has a World Cup championship and he had a fling with model Ariadne Artiles.

    He literally could die having accomplished everything he set out to do in life. After Artiles, there is absolutely nothing else.

34. Dennis Rodman and Vivica A. Fox

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    The weird angle must really work on women because in 1997, Fox and Rodman were hooking up.

    I would have to douse myself in Purell if I was just in the same room as the man. 

33. Alex Rodriguez and Madonna

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    This fling came out of nowhere in 2008. Just as the Rodriguez was finalizing his divorce, rumors circulated that the Yankee was having a a torrid romance with Madonna.

    The pairing was a bit odd as Madonna is looking more like a mummy and less like a pop star as of late. 

32. Lance Armstrong and Ashley Olsen

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    The odd pair were rumored to have hooked up in 2007.

    Here is Ashley in her Sunday best, or is that Mary Kate?

    You know what, it doesn't matter. 

31. Andy Roddick and Paris Hilton

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    America's number one tennis pro was caught volleying with the heiress back in 2006, if you know what I mean.

    They were dating, for those who are inept at the fine art of subtlety. 

30. Tara Reid and Jeremy Shockey

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    I really could have picked any NFL player here. Reid has been linked to many men of the gridiron.

    Sadly, no placekickers were rumored, though. Those guys just can't seem to snag any tail. 

29. Jason Kidd and May Anderson

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    After Jason Kidd divorced Joumana, he immediately prowled the streets for his first girlfriend.

    He found model May Anderson. They didn't last long but she was only a rebound anyway. 

28. Shakira and Rafa Nadal

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    The Latin booty shaker was rumored to be seeing Rafa Nadal.

    Here she is cooling off that hot body of hers. 

28a. Kobe Bryant and Brandy

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    Tying Shakira and Rafa Nadal for singer-athlete love is Kobe Bryant and Brandy. She was nice enough to go with him to his prom. 

    I have this star-studded couple so low because there is no way prom flings are as hot as post-college flings. That is just science. 

27. Brian Urlacher and Paris Hilton

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    The two were seen canoodling at a game in 2004.

    Canoodling was so "in" in 2004. I never got the finer points of that practice down, unfortunately. 

26. Andy Roddick and Mandy Moore

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    Mandy Moore should be a lot more popular. Her combination of innocence and sex appeal is second to none. Why has she not been in anything but horrible movies? Please Hollywood, get her a good movie for me to watch. 

25. Alex Rodriguez and Kate Hudson

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    The future Hall of Fame Yankee dated the stunning Kate Hudson for a brief time in 2009. She must have looked the other way on the whole cheated-on-his-wife, not-to-mention-the-nation's-pasttime thing.

24. Maria Kirilenko and Rafa Nadal

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    Two of tennis's top performers were rumored to have been more than just colleagues for a bit. That is more than enough reason to include this hottie. 

23. Brad Penny and Alyssa Milano

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    Brad Penny and my favorite girl of all time were dating while he was pitching for the Dodgers. Well, he wasn't exactly pitching for the Dodgers so much as he was walking batters and genuinely being ineffective.

    Either way, they dated. 

22. Kobe Bryant and Katelyn Faber

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    Kobe Bryant had an affair with 19-year-old Colorado hotel employee Katelyn Faber in June 2003. Faber then accused Bryant of non-consensual sex. Faber never appeared in court to make her claim and Kobe Bryant has since been resurrected from those dark days. 

    There is little on the Internet in the way of photos of Faber. I include a picture of the seemingly happy married couple, Kobe and Vanessa Bryant. 

21. Carmen Electra and Dennis Rodman

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    The couple married in November 1998. We were sure that these two would be the face of matrimonail bliss for years to come. 

    Unfortunately, we were all proved horribly wrong when they split five months later. 

20. Derek Jeter and Jessica Alba

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    Derek Jeter dated the Hollywood starlet and gave her a little more than she bargained for. Go ahaed and google the two names and see what you get. 

    Please gentlemen, practice safe flings. 

19. Tiger Woods and Rachel Uchitel

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    Rather than sit here and list off the dozen or so flings Tiger Woods had, I will use his hottest one as a placeholder for all of Tiger's women. 

    That brings me to the subject of a new reality show I am pitching. It's called Tiger's Women and it stars all of his past triumphs. The winner has to fight Elin Nordegren in the final episode. It is a mix between Spike's The Ultimate Fighter and Basketball Wives.

    What do you think?

18. Mark Sanchez and Jamie-Lynn Sigler

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    The two were dating for a bit this past summer. They looked like they would have made a nice couple.

    But there is no reason to lock yourself in to a long relationship when you are Mark Sanchez. 

17. Tony Parker and Erin Barry

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    If you have been lost at sea or in a coma for the past week, Tony Parker and Eva Longoria are divorcing. In the middle of it all is news that Parker was sexting Mrs. Brent Barry.

    That's a fine way to treat a former teammate. 

16. John Terry and Vanessa Perroncel

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    I just have to give flings a boost when their is a scandal involved. This was one of the bigger scandals in sports until Tony Parker decided to text romantic suggestions to a former teammate's wife. 

    John Terry, the defensive back for English giant Chelsea, had an affair with Vanessa Perroncel. She was dating former teammate Wayne Bridge at the time.

    The affair cost Terry the captaincy of the English national team. 

15. Jason Kidd and Gabrielle Union

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    Jason Kidd dated Gabrielle Union for a short while. She is now rumored to be in the loving embrace of Dwayne Wade.

    No matter who she roots for, she is smoking hot. 

14. Chris Webber and Tyra Banks

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    Chris and Tyra were dating for a spell before Chris called time out on the whole thing.

    Do you see what I did there? Do you?

    I do it for you. 

13. Brad Penny and Eliza Dushku

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    I have no idea what it is with Brad Penny. But the guy gets women, and really hot ones. I mean he is a fat overrated pitcher that can't stay on one team.

    I don't see it. Does the guy just have really big, um, feet?

13. Tony Romo and Carrie Underwood

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    It seems Tony Romo did not have his fill of sultry singers.

    He dated Carrie Underwood for a hot minute after his long relationship with Jessica Simpson. 

12. Barry Zito and Alyssa Milano

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    Being a Dodgers fan I am not the least bit upset that Ms. Milano sunk to the level of Barry Zito.

    I think we all make mistakes in life. This was hers. 

11. Cristiano Ronaldo and Maria Sharapova

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    Before there was the backup Lakers guard Sasha Vujacic in her life, there was Ronaldo.

    I leave it to you to decide if she traded up or down. 

10. Matt Kemp and Rihanna

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    The couple were hot and heavy for a few months of the season.

    Kemp was so smitten that he forgot how to play baseball for the duration of their fling. 

9. Matt Leinart and Britney Spears

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    Back in 2006, Britney Spears was seen getting all nasty with Matt on the dance floor.

    I think the sight of both of them with anyone is nasty, so there. 

8. Reggie Bush and Kim Kardashian

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    I had to include the months that Kim dated the Saints running back. If only to include another picture of the beauty in the list. 

    The two were so on again off again; I am sure it felt like a fling every time. 

7. Derek Jeter and Scarlett Johansson

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    The two had a quick romance in 2004.

    That would make it official: Jeter has dated the hottest women on the planet. He is my god. 

6. Tony Romo and Sophia Bush

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    The Cowboys star just can't seem to catch a break in the ladies department. He seems to get his heart broken at every turn.

    I feel so very, very bad for him. 

5. Kim Kardashian and Miles Austin

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    It looked like the real deal. These two looked like they were in it for the long haul.

    Actually, I knew it would just be a summer fling. 

4. Mark Sanchez and Hilary Rhoda

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    If Mark Sanchez didn't already have it all, he has been linked with Sports Illustrated model Hilary Rhoda. She is making me feel a little funny. 

3. Derek Jeter and Mariah Carey

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    Derek Jeter started off his career with a bang. He was the starting shortstop with the most storied franchise and he was dating the hottest pop singer at the time. 

    You know what? Mariah is still hot. There, I said it. 

2. Kristin Cavallari and Matt Leinart

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    The hot reality star hooked up with Matt Leinart when he was still relevant.

    Now she is dating an actual starting QB in Jay Cutler. 

1. Derek Jeter and Jessica Biel

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    The one thing I admire more about Derek Jeter than his ability to collect unwarranted Gold Glove awards is the level of women he gets. 

    Jessica Biel is one of the hottest women in the world. For Jeter, it was just one more notch in the bed post. 

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