Stephanie McMahon isn't an in-ring specialist by any stretch of the imagination, but sge relishes a challenge and will take care of her business inside the squared circle. One of the most powerful women in WWE history, Stephanie McMahon won't be remembered for her matches inside the ring. She will be remembered for being an exceptional heel, and a member of the McMahon family.The Billion Dollar Princess is the daughter of WWE Chairman Vince McMahon, and she is the wife of Triple H. Stephanie was introduced to wrestling fans in 1999 during the height of the Attitude Era. She was a babyface, but at Armageddon 1999, she turned heel and formed a legendary alliance with Triple H. During the early stages of her career, Stephanie wrestled in a handful of matches. She was not cut out to wrestle, but she did give it her all. The Billion Dollar Princess did manage to have some entertaining matches and abused her power to gain the advantage in some clashes.
10 Stephanie McMahon & Shane McMahon Vs. Lita & Big Show - Raw (7/24/00)
On the July 24, 2000, edition of Raw, Stephanie McMahon and her brother Shane made history as the first brother and sister pairing to battle in a tag team match. They were up against Lita, and her surprise tag team partner Big Show.
Shane wasted no time and ran like a scolded dog when Show made his way down to ringside. The match was ruled as a no contest, and Lita took advantage of the inexperienced Stephanie. Lita's rival Trish Stratus came down to ringside, and Stephanie and Trish battered Lita with vicious strap shots to the back.
9 Stephanie McMahon Vs. Lita - SmackDown (6/8/00)
Stephanie McMahon defended the WWE Women's Championship for the first time on the June 8, 2000, episode of SmackDown. Lita won a battle royal earning the right to face Stephanie for the Women's Title. However, it was a ruse as Tori assaulted Lita from behind, and executed her patented powerbomb.
Tori was the special guest referee, and Stephanie asked for the bell to be rung. The Billion Dollar Princess took advantage, and she pinned Lita to successfully defend her Women's Championship.
8 Stephanie McMahon Vs. Lita - Raw (6/12/00)
Four days later, Stephanie McMahon had another Women's Championship title defense against Lita on the following episode of Raw. There was a caveat as McMahon would be stripped of the Women's Title if anyone from the McMahon-Helmsley faction intervened.
That was music to Lita's ears, and she knocked Stephanie off the apron. McMahon feigned a knee injury with Kurt Angle sneaking up behind Lita. Angle planted Lita with the Olympic Slam. Stephanie got back up on her feet, and she pinned Lita to retain the Women's Championship once again. Stephanie and Angle began celebrating in the ring with Triple H applauding in the locker room.
7 Stephanie McMahon & Test Vs. Debra & Jeff Jarrett - Raw (9/20/99)
The September 20, 1999, edition of Raw featured Stephanie McMahon's in-ring debut. She teamed up with her on-screen fiancee Test and they battled Debra and male chauvinist Jeff Jarrett, who was also the Intercontinental Champion.
Test decimated Jarrett with ease, and Jarrett had no answers for Test. Stephanie didn't get involved in the match until the latter stages. After Test did all the work, he tagged in Stephanie, and she embarrassed Jarrett by pinning him to pick up her first victory.
6 Stephanie McMahon Vs. Jacqueline - SmackDown (3/30/00)
Stephanie McMahon challenged Jacqueline for the WWE Women's Championship on the go-home episode of SmackDown before WrestleMania 2000. This was her first singles match, and to go for the Women's Championship isn't bad.
McMahon acted terrified, but she was in safe hands as her husband Triple H and the rest of DX accompanied her to ringside for moral support. Jacqueline was outnumbered, and Tori planted Jacqueline with a DDT. Stephanie pinned Jacqueline to win the Women's Championship which saw Stephanie and Triple H cement their spot as the power couple in WWE.
5 Stephanie McMahon & Kurt Angle Vs. Lita & The Rock - SmackDown (8/24/00)
Stephanie McMahon and Kurt Angle were out for revenge on the August 24, 2000, edition of SmackDown. They collided with new Women's Champion Lita and WWE Champion The Rock in a mixed tag team match. The bout started on the outside before the bell even sounded. Lita executed a hurricanrana on Stephanie. Moreover, Stephanie slapped The Rock in the face when he applied the Sharpshooter on Angle.
The Rock pushed Angle into Stephanie, and she fell first-face into the steel steps. Triple H ran down the aisle, and he carried his wife into the locker room. Triple H returned to the ring, and he assaulted The Rock and the referee. The Rock and Lita prevailed by disqualification. However, Angle kissed Stephanie in the locker room.
4 Stephanie McMahon, Triple H & Kurt Angle Vs. Trish Stratus And T&A - Raw (9/18/00)
On the September 18, 2000, episode of Raw, Triple H, and Kurt Angle put their differences aside. They teamed up with Stephanie McMahon, and they collided with Trish Stratus and T&A in an intergender six-person tag team match. It wasn't an instant classic but Triple H and Angle managed to work as a cohesive unit.
Stephanie and Trish brawled with Trish gaining the upper hand. Test was going to finish off Stephanie with an elbow drop from the top rope. However, Triple H intervened by pushing Test off the top rope. Triple H executed the Pedigree on Test, and Stephanie pinned her former fiancée for the victory.
3 Stephanie McMahon & Triple H Vs. Trish Stratus & Kurt Angle - Raw (1/22/01)
Twenty-four hours removed from the 2001 Royal Rumble, Stephanie McMahon and her husband Triple H were in mixed-tag team action. Trish Stratus and WWE Champion Kurt Angle were on the other side of the ring. This was a fun contest with both teams having a lot of offense.
Angle rammed Stephanie to the ground, but that proved to be unwise as she slapped him and Triple H gave him some right hands. The action spilled onto the outside with Angle and Triple H continuing their fight. Ultimately, Triple H laid out Trish with his trademark Pedigree, and Stephanie covered Trish for the win.
2 Stephanie McMahon, Triple H & Kurt Angle Vs. Lita & The Dudley Boyz - SmackDown (8/3/00)
Stephanie McMahon, Triple H, and Kurt Angle were on the same team on the August 3, 2000, edition of SmackDown. They were up against Lita and The Dudley Boyz. This is an underrated intergender no disqualification match. There were tons of action but Triple H and Angle had their issues, and still managed to work as a cohesive unit.
Stephanie and Lita were left to their own devices with Lita getting the upper hand. Bubba Ray Dudley attempted to put Stephanie through the table but Angle and Triple H halted that from happening. Nonetheless, Triple H's Pedigree on Lita was the difference maker as Stephanie got the bragging rights for her team.
1 Stephanie McMahon Vs. Lita - Raw (8/21/00)
Lita challenged Stephanie McMahon for the Women's Championship for a third time on the August 21, 2000, edition of Raw. Stephanie made her way toward the ring with her husband Triple H and Kurt Angle by her side. Reigning WWE Champion The Rock was the special guest referee.
There was a big fight feel to the match, and the two women closed out the show. Lita dominated the match, but Stephanie didn't go down without a fight. The Billion Dollar Princess' lackluster Women's Title reign came to an end with Lita finally dethroning Stephanie.