Stephanie McMahon’s 10 Most Memorable WWE Matches

5. Stephanie vs. Jacqueline - SmackDown (March 30, 2000)

https://www.youtube.com/watch?v=hhrUlrmZ5v8 With WrestleMania 2000 just days away and tensions between the McMahon family at their height, Vince looked to punish his ungrateful, bratty daughter Stephanie by booking her in only her second official match. Her opponent? The double-tough Women's champion Jacqueline. Surely the chairman was expecting the Dallas, Texas native to unleash a can of ass whooping that Steve Austin would be proud of, teaching his youngest a lesson in respect and discipline along the way. As history tells us, that was not the case. Sure, Jacqueline got a few shots in on the Billion Dollar Princess but interference from the villainous vixen Tori assisted Stephanie in not only defeating the veteran performer but also capturing the gold, much to the dismay of her father and fans watching worldwide. With only three days until the biggest show of the year, the McMahon-Helmsley Regime possessed the most important titles in men and women's wrestling and Stephanie was well on her way to become one of the most hated characters in all of sports-entertainment. Her title reign would last five months and with every passing week, fans grew more and more irritated with the spoiled young woman's grip on the championship. Luckily, a fiery redhead with a never-say-die attitude and a move set rivaling that of her male counterparts would arrive to save the day and bring legitimacy back to the title. Which brings us to...