Tiger Woods Vs Michael Phelps: The 10 Most Attractive Women Each Man Hooked Up With

Hello and welcome to another versus edition here on The Sportster. In this monumental clash, we take a look at the impressive resumes of both Michael Phelps and Tiger Woods. Now we’re not talking about their sports resumes; instead, we dive in a little deeper taking a look at their personal histories pertaining to hookups from the past. Close the door, cause things are about to get “Not So PG”. Are you ready?!

For Tiger, his hookup formula is quite simple: blonde & busty, thank you very much. As for Phelps, he’s changed things up going for a more “variety” based approach. Each formula is quite sound so prepare to drool in this clash.

From adult stars, to models to athletes, we’ve truly got it all in this article as the two titans collide. Please, let us know who you believe is the winner of this contest via Facebook, it’s just too close to call for our experts here on The Sportster. Enjoy the article and be sure to share it with a friend so he can join in on the fun. Without further ado, here are ten of the hottest women Michael Phelps and Tiger Woods have hooked up with. Ring the bell, let’s get started! Tiger, you start!

20 Tiger Woods – Lindsey Vonn

In every one-on-one encounter, the start is absolutely crucial, now look, we’re all suckers for a good comeback but starting off on the right foot is essential and that’s exactly the case in this article as we start the list off with one of steamiest females of all, one Lindsey Vonn.

Of course, the two did a lot more than just “hookup”, they also dated for a couple of years and seemed to be quite happy. Vonn still has nothing but respect and admiration for Woods despite the break up, we have reason to believe the feeling is mutual for Tiger. Since the two broke up, Vonn has upped her game dropping jaws on the regular. This recent pic you see above posted on her Instagram has us in amazement at how hot someone can actually look in a ski suit. Well done Lindsey and, well done Tiger.

19 Michael Phelps – Stephanie Rice

Okay, so Tiger just landed a big one, but Michael Phelps knows a thing or two about a good old fashion comeback, he lands a big blow right back to Tiger with this hookup staying in his field of work. According to the gossip mill, Phelps and Stephanie Rice had a brief fling relationship in the past. Both are swimmers, so it isn’t too hard to figure out how they met. Phelps scores some huge point for this one as Rice looks more suited as a fitness model than an actual swimmer. Just imagine how lean their kids could have been?

Take a quick scroll at Rice’s Instagram page and you’ll certainly be clicking the follow button without hesitation. She’s got a couple of “Not So PG” like photos, but in truth, her sheer beauty alone is good enough.

18 Tiger Woods- Cori Rist

via zimbio.com

Party girl, lingerie model, whatever you want to call her, Cori Rist is one smoking hot chick. They two met back in Tiger’s wild nights out on the club. The catch here, both were married at the time. Looking at Rist, she most certainly fit the bill in terms of what Tiger was seeking out of his women which was quite simple, a beautiful blonde with some fantastic assets. Rist fit the bill to a tee.

The relationship caused quite the storm however; Rist’s ex-husband took to the media claiming Tiger went as far as to make money transfers to Rist at one point in time. Things continued to get exposed when Rist showed up on an Italian talk show to tell all about the situation. All the twistedness aside, she’s a smokebomb and one of the very best when it comes to Tiger’s prior hookups.

17 Michael Phelps - Win McMurry

via blogspot.com

We have reason to believe this is a huge shot fired at Tiger Woods and likely, the biggest blow in the encounter thus far. This one hurts for two reasons; one, Win is a smoking hot blonde, which is what Tiger loves. But even worse than that, McMurry is a golf personality that loves the game dearly. We believe Tiger would have taken this beauty to the “back nine” if given the chance, but it turns out Phelps beat him to the punch, landing a devastating blow.

The two were revealed as an item back in 2013 when Phelps brought the blonde beauty to the ESPYS. According to the rumors, the two shared a brief relationship. Both have now moved on as McMurry enjoys the family life away from the spotlight that is Michael Phelps.

16 Tiger Woods - Joslyn James

via express.co.uk

Okay, so Tiger got rocked a bit. He started off on the right foot with Lindsey Vonn but Phelps just fired on hell of a bomb with one of the hottest females involved in the game of golf. Tiger’s reeling a little, but he now gets up, dusts his shoulder off and unveils one Joslyn James as the next mistress on the list. When someone from the adult industry gets pushed into forefront, you know its game on folks!

As you see in the photo above, James has a certain pair of assets that are quite noticeable. Looking at Tiger’s track record, he’s a fan of women that are “blessed in the chest”. It seems like James was doing all the right things as the two had an affair lasting three years if you can believe. Along with the “Not So PG” bedroom antics, Woods is said to have been quite the trash talker via text messages....

15 Michael Phelps - Taylor Lianne Chandler

via youtube.com

Okay, so Phelps for some reason doesn’t seem too rattled by that recent Tiger hookup entry, why you ask? The answer is simple, Phelps hooked up with an adult entertainer himself - oh yes, we’re talking about the veteran adult star Taylor Lianne Chandler. Oh, and like James, she has a certain pair of “Not So PG” assets that are also quite “blessed” thanks to a little surgery. Phelps is smiling, while Woods is searching for Taylor’s email.

So Phelps responded quite nicely, but the relationship was the exact opposite. Chandler became obsessed over the swimmer and she took to social media following the end of their “Not So PG” antics. Heck if you go on her website, she even says she hooked up with the guy, yikes! Chandler unveiled lots of personal info including a private picture of Phelps’ junk. For all those headaches, this hookup isn’t as glamorous, and maybe, one Michael wishes never took place. Stop pointing and laughing Tiger.

14 Tiger Woods - Holly Sampson

via nydailynews.com

So Tiger’s feeling a lot better about himself in this clash as Phelps just dropped the ball with his prior hookup given the way it ended. Woods looks to take advantage of that with another stunner from the adult industry, Holly Sampson. In truth, Woods just landed a “Stone Cold Stunner” with this busty babe from his past. Again, “blessed in the chest” is another obvious theme for Tiger and his love of the adult stars he previously hooked up with.

Like the others, Sampson took to the press when talking about her experience with the golfer. According to Holly, the encounter was quote “amazing”, last 45 minutes. Now that’s 44 minutes longer than the average human being.... With such positive feedback and hooking up with such a smokebomb, Tiger takes the lead in this clash!

13 Michael Phelps – Maria Ho

We now see a visual of Phelps cooling off in a swimming pool doing a couple of laps at a slow pace. He’s trying to regroup and get back into this encounter. He now raises from the water and starts to walk on it.... we look at him in silence as he whispers the name, Maria Ho. Phelps is back in the clash.

The beauty of this prior hookup is the rarity of it all. It’s not every day someone hookups with a popular poker player, but that’s exactly what Phelps did back in 2008 when the two met out and about in Vegas, while of course, partying it up. Looking at the recent picture above taken from Ho’s Instagram, Michael scored big time with this poker goddess.

12 Tiger Woods - Loredana Jolie

via flickr.com

We now get a glimpse of Tiger pulling a slow clap while smiling, he’s got something up his sleeve and that something is one Loredana Jolie, a former Playboy model. Front and back, this blonde bombshell has it all going on. Jolie even admitted to flirting with Michael Jordan back in the day, so yea, you can say this chick has got some serious game as well.

Jolie actually wrote a book on her experiences with athletes, of course, the most high profile came with Tiger Woods as she opened up about the experience. According to Jolie, Tiger was wild and took things to another level, she recalls the two going at it from nine at night till the wee morning hours of the next day, she called his intercourse fantasies “not normal”. Looking at Jolie, you can’t blame the golfer for “going all in”. Maria Ho is shaking her head somewhere reading that.

11 Michaels Phelps - Brittny Gastineau

🌺🌺🌺🌺 #glam @angiiee_maartinez @blushington 📸 @lisagastineau

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Phelps scores a bomb in this encounter, one he needed desperately. What makes Gastineau so unique is the fact that she’s a brunette busty bombshell, something that is unlike most of Tiger’s hookups that feature the busy blonde most of the time. Major props to Phelps for changing it up in terms of his “flavors”, sorry Tiger.

Known as Britt, the beauty serves as a model, actress and host. She’s also BFF’s with Kim Kardashian, which like, isn’t too shocking given her physical appearance which is quite close to Kim’s in truth. The two shared a low key romance back in 2010, things got seriously out of hand, so much so that the rumor mill made the claim that Britt was pregnant with Michael’s kid! Of course, that allegation proved to be false.

10 Tiger Woods - Kristen Smith

via thesun.co.uk

Another blonde, this time shaped similar to his ex-wife, we now welcome to the podium one Kristen Smith, aka, Tiger’s latest girlfriend. She works as a stylist, which helps so she could give Tiger some advice to wear something that doesn’t have a damn check mark on it. She was also married to a former NFLer, a Dallas Cowboy, Gerald Sensabaugh.

Following Tiger’s arrest for being found passed out in front of his wheel, things went south between the two and it’s unclear if they remain a couple at this point. Smith made the headlines as her reaction to Tiger’s arrest was well documented by the paparazzi. Not only was she infuriated, but she went on a massive shopping spree, likely funded by yours truly, Sir Tiger Woods. For the first time in this clash, Woods gets a harsh blow because of the backlash pertaining to this hookup/girlfriend.

9 Michael Phelps – Carrie Prejean

Phelps smells blood with Tiger’s recent entry; he lands a solid right to the temple of Woods with this shattering hook up of a former Miss USA from 2009. To make matters worse, as you see in the Instagram picture above, Carrie is blonde, beautiful and something Tiger also loves, pretty darn busty both front and back. Tiger really doesn’t care about the blow, he’s too busy creating an Instagram account so he can DM the beauty. The message likely reads, “In rehab, got a break soon, you free, it's Tiger”.

The relationship was unclear as many believe the two just had a brief hookup, both denied the relationship was serious despite being spotted together at various parties, including an outdoor beach party. Nonetheless, relationship or not, Michael scores huge points for this one.

8 Tiger Woods – Jaimee Grubbs

via twitter.com

Woods loved the nightlife, and it is there where he met this beautiful cocktail waitress in one Jaimee Grubbs (she was a dirty blonde, so he stuck to his guns). The two shared a 31 month relationship, which is pretty absurd given the plethora of other secret long-term relationships he withheld in the past. How Tiger didn’t know he was going to get caught is truly beyond us, but hey, we digress.

Tiger was extra naughty in this secret affair as he used his cell phone as a “Not So PG” tool when talking to Grubbs. Jaimee unveiled several “Not So PG” text messages some of which were just truly absurd. Things went downhill for Grubbs following the leaked affair as she got arrested and hit a little bit of a struggle.

7 Michael Phelps – Caroline Pal

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Phelps is now starting to tease Tiger a little bit as he showcases a cocktail waitress of his own in Caroline Pal. The message is clear here, anything you can do, I can do better according to Phelps (he never said that, we’re just having fun in case you haven’t noticed).

Pictures of the two spread like wildfire back in 2008 as they were spotted at various hot spots, including a specific beach party where the two got pretty intimate. The relationship was more than a fling as the two took a liking for one another. Of course, back then, Phelps was riding a high coming off the Olympic Games so you can bet his confidence was pretty sky high. Big blow by Phelps once again, how will Tiger respond as tables seem to be turning?

6 Tiger Woods - Rachel Uchitel

via extratv.com

On the surface, Woods scores some major points given Rachel’s clear beauty. However, looking at the way things would unfold, once again, Woods loses some points in this clash. Why you ask, let us explain.

Back in 2009, Tiger’s life changed forever because of the relationship with Rachel. The National Enquirer ran a story about the infidelity, and landed Woods in some serious hot water. Things went from bad to worse when Tiger’s wife caught Rachel texting her former husband. From then on, things just unravelled.

Tiger’s numerous affairs would come out following the incident. Rachel was recently asked about Tiger and she finally started, “she no longer cares about him”. It took eight years since the incident, but it’s nice to know she’s finally moving on with her life, while poor Tiger, is reading this from a rehab center.

5 Michael Phelps - Megan Rossee

via nydailynews.com

Because of the backlash caused by Tiger’s past flings, he’s taken some stiff jabs in this encounter after he started off so darn well. The advantage is clearly with Phelps at this point and he adds to his lead with this crushing blow of a past romance from back in the day with the stunning Megan Rossee who can be considered one of the hottest smokebombs on the entire list. Blonde, slim and facial features of a goddess, we drool at his past hook up and wonder how in the hell Phelps let her go.

Turns out youth was the reason, both were still young as the relationship took place years ago. In addition, both felt as though the relationship wasn’t really going anywhere. Nonetheless, major points go to Phelps for this past hook up, Tiger’s in bad shape folks!

4 Tiger Woods - Elin Nordegren

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We now put our focus on the most intimate partners both have ever had, we start with Tiger and his ex-wife, Elin Nordegren. The two met way back in 2001 for the first time and later, would get married and start a family together from 2004 till the bitter end in 2010. Born in Stockholm, Sweden, Elin is beautiful both inside and out. Tiger was a lucky man and he made decision he’ll live to regret in all likelihood.

Nowadays, with her massive settlement money, Elin is leaving a quiet life away from the public spotlight as she watches her former man continue to crumble. In a surprising announcement by Woods himself, the two are still on great terms, and enjoy friendly conversation with one another. We’re really not sure how to react to that....

3 Michael Phelps – Nicole Johnson

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We now switch gears to Phelps’ current wife, the beautiful and stunning Nicole Johnson. We believe Tiger doesn’t care all that much given the fact that Johnson is a brunette, but given her beauty, even she can turn Tiger.

The former Miss California 2010 started dating Michael a couple of years back and they would end up getting engaged in 2015. They went through a struggle from 2009 till 2014, going on and off but they worked at things and ended up getting married in May of 2016. Both are now enjoying life as proud parents. It looks like the days of Michael's hookups are done for, we applaud his resume and wish him the best in his new life as a happy papa.

2 Tiger Woods – Laci Kay Somers

Come on Barbie let's go party💚 🎉 @imlacikaysomers

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Both combatants need a massive bomb to close out this clash and that works double for Tiger given the recent entries on the list and the controversy they carried. Woods rises from the ashes and lands arguably the biggest blow of the entire clash as he truly saves the best for last. Brace yourself Michael, we now introduce a rumored Tiger hookup, ladies and gentleman, we present to you, Laci Kay Somers. Tiger just threw his golf club in the air and walked away as if he just won the clash. Do you blame him? Nope.

The bombshell has close to nine million followers and let’s just say it isn’t because of her captions. Somers can have you scrolling for days with those “Not So PG” photos. She’s got every single asset going on, all we have left to say is... damn you Tiger, damn you.

1 Michael Phelps – Lily Donaldson

Behind the scenes at my @gap vintage denim fitting. Reviving and upcycling. #GapforGood

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Phelps took a hard one and some might believe he lost the clash with Lacy Kay Somers sticking in the final blow. However, Phelps isn’t going out quietly as he introduces a beauty with millions of followers of her own along with serving as a Victoria Secret Model, of course, we’re talking about Lily Donaldson!

Lily is legit perfect, her darn stomach is so lean it looks like it was sculpted. It really depends on personal preference at the two are beautiful in their own ways, which makes the clash that much more unique. Phelps and Lily had a brief romance back in 2008 and if he was single, there’s no doubt he’d be sneaking into her DMs!

So there you have it folks, this one is too close to call. Let us know who won this monumental clash between these legendary sports figures!

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