“Tiffy Time” has been taking over WWE. Tiffany Stratton has, without a shadow of a doubt, everything that it takes to be one of the faces of the company. Despite only being involved in professional wrestling for a few years, she has already shown that she can hold her own against anyone.
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And as the former women’s Money in the Bank contract holder, she waited patiently before she cashed-in. Eventually, she chose her moment and became WWE Women’s Champion. While Stratton has been in WWE for only a few years, she has shown a constant evolution. With all of that being said, let’s take a look at Stratton’s evolution over the years.
UPDATE: 2025/03/08 17:30 EST BY BENJAMIN VIEIRA
After months of waiting, Tiffany Stratton cashed-in her Money in the Bank contract to become WWE Women’s Champion in January of this year. It was a moment that many fans had wanted to see. She organically went from being a heel to a babyface as she proved that not only was she great at character work but also as a major force in the ring. Stratton has shown that she will be a name that carries WWE for years to come. However, she faces a major hurdle with a match against Charlotte Flair at WrestleMania 41. But, for now, let’s look at Stratton’s WWE journey so far.
“Tiffy Time” Began In 2021
She Previously Competed In Gymnastics
- Stratton’s PC class also featured Solo Sikoa.
- Her real name is Jessica Woynilko.
- She had no experience wrestling before WWE.
After spending time pursuing gymnastics, Stratton decided to take a leap and pursue a career in WWE. It all began with Stratton signing with NXT in 2021. She was a part of an NXT Performance class that also featured Solo Sikoa.
It was Stratton’s first entry into wrestling. As history has shown, it is a field that she has thrived in so far.
She Debuted Against Amari Miller
Stratton Won Her First Match
- Stratton debuted with a spoiled, rich girl gimmick.
- She battled Amari Miller on November 16, 2021.
- The match lasted under four minutes.
Stratton had her very first-ever professional wrestling match on November 16, 2021. Before it was “Tiffy Time”, she was another wrestler trying to prove herself in NXT. She also had a spoiled, rich, “daddy’s girl” gimmick.
On an episode of 205 Live, Stratton managed to pick-up a win over Amari Miller.
Stratton Makes Strides In The NXT Women’s Breakout Tournament
She Was A Replacement For Nikkita Lyons
- Lyons dropped out due to injury.
- Stratton defeated Fallon Henley in the semi-finals.
- She lost to Roxanne Perez in the finals.
In 2022, Stratton was featured as a part of the NXT Women’s Breakout Tournament. However, she was not initially supposed to be in it. Stratton was a replacement for Nikkita Lyons, who had sustained a serious injury that kept her out of action for a long time. But, Stratton made the most of her opportunity.
Stratton was able to defeat Fallon Henley to make it to the finals. There, she faced Roxanne Perez. However, she ended up losing the match. But, it did not derail Stratton. She actually was able to grow more and more.
Stratton Battled Wendy Choo
It Was One Of Stratton’s Stand-Out Matches
- The two battled twice.
- Stratton picked up the first win.
- Choo won Lights Out.
One of Stratton’s biggest stand-out performances came when she entered a rivalry with Wendy Choo. Initially, Stratton had picked up a win over Choo. But, it was not the end of their feud.
Choo and Stratton battled in a Light Out match. It was a match-up that was no disqualification and everything goes. Again, while Stratton did lost the bout, she looked very strong throughout the match. Despite taking these losses, they never made Stratton look weak in defeat.
Stratton Reached The Top Of NXT
She Won The NXT Women’s Championship
- Stratton made changes to her gimmick.
- She won the NXT Women’s Title at Battleground 2023.
- She defeated Lyra Valkyria.
After months of proving herself and evolving her character. She dropped the “daddy’s girl” aspect and instead built herself up to be more braggadocious and get what she wanted. Stratton was able to do that when she finally reached the pinnacle of NXT.
At NXT Battleground 2023, Stratton defeated Lyra Valkyria to capture the NXT Women’s Championship. It was a tremendous moment for Stratton and one that had truly solidified her as one of WWE’s biggest rising stars.
Stratton Goes To War With Becky Lynch
The Present Meets The Future
- Stratton held the title for 107 days.
- She made a few successful defenses.
- Lynch defeated Stratton to win the title.
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While Stratton did not hold the title for too long, it was nonetheless a memorable one. She successfully retained it against Thea Hail and Kiana James. However, her greatest rivalry came when she battled with Becky Lynch.
Lynch actually managed to defeat Stratton to win the title. But, that was not the end of their feud. At No Mercy 2023, Stratton and Lynch went to war in an Extreme Rules match. It was a match that was praised by fans and critics alike.
“Tiffy Time” Goes To The Main Roster
She Debuted On The Main Roster
- Stratton entered the women’s Royal Rumble at 29.
- She eliminated Roxanne Perez.
- Stratton was eliminated by Bianca Belair and Bayley.
After feuding with Lynch, and a brief rivalry with Fallon Henley, Stratton was ready to make the jump to WWE’s main roster.
At the 2024 Royal Rumble, Stratton entered the women’s Royal Rumble match at number 29. Before being eliminated herself, Stratton managed to throw Roxanne Perez out of the match.
She Entered The Elimination Chamber
Stratton Was Signed To SmackDown
- Stratton defeated Zelina Vega to qualify for the Elimination Chamber.
- The match also featured Naomi, Raquel Rodriguez, Bianca Belair, Liv Morgan, and Becky Lynch.
- Lynch was the winner of the match.
Upon her arrival on the main roster, Stratton was signed to SmackDown. And, she wasted no time in establishing herself. Through a win against Zelina Vega, Stratton qualified for Elimination Chamber: Perth.
Stratton put up an incredible performance in the match. But, she did not win. Nonetheless, this did not slow her down. In fact, it was only a matter of time for Stratton.
Stratton Becomes Ms. Money In The Bank
She Earned A Guaranteed Shot At Gold
- The match took place in Toronto, Ontario, Canada.
- Stratton, Lyra Valkyria, Chelsea Green, Naomi, Zoey Stark, and IYO SKY were all in the match.
Stratton put herself into the WWE Women’s Championship picture. And despite some failed attempts to get the title, they did not derail her. But, her time finally came at Money in the Bank.
Stratton, who was one of the favorites heading into the match, captured the women’s contract. She climbed the ladder and captured her future instantly.
Reaching The Tiffy Top Of WWE
Stratton Became WWE Women’s Champion
- Stratton cashed-in on Nia Jax.
- She won the title on January 3, 2025.
- She has held the title for over 60 days.
For months, WWE teased that Stratton was going to turn on her longtime ally, Nia Jax. On January 3, 2025, she executed one of the greatest cash-ins of all-time. After it was all said and done, Stratton walked out with the WWE Women’s Championship. After less than a year on the main roster, she reached the top of the mountain in the company.
So far, she has had successful defenses against Nia Jax and Bayley.
Trishy And Tiffy Time Takeover Toronto
They Teamed Up At Elimination Chamber
- Stratton teamed up Trish Stratus.
- They faced Nia Jax and Candice LeRae.
- Stratton and Stratus were successful.
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The two took on Nia Jax and Candice LeRae in a tag team match and were successful in defeating Stratton’s former allies.