In 1991, Wippleman debuted in the World Wrestling Federation (WWF) as a manager. He first managed Big Bully Busick. When Busick left the company and Slick turned face, Wippleman took over managing The Warlord. However, Wippleman's greatest acquisition was Sid Justice. When Sid turned heel, working on a program with Hulk Hogan leading to WrestleMania VIII, Wippleman became Sid Justice's manager and became Dr. Harvey Wippleman. Wippleman would begin carrying a doctor's bag to the ring containing medical equipment. After Sid's matches against jobbers, Wippleman would retrieve a stethoscope from his bag and listen to the defeated wrestler's hearts.
After Sid left the company, Wippleman managed Kamala, who was feuding with The Undertaker. After Kamala was defeated by Undertaker in a coffin match at Survivor Series in 1992, Kamala left Wippleman and Reverend Slick became his new manager. Afterwards, Wippleman dropped the doctor gimmick. He continued to feud with the Undertaker and brought a new wrestler to the WWF, the nearly eight-foot-tall Giant González. The feud culminated in a Rest in Peace match at SummerSlam, which Undertaker won. During this period, Wippleman also briefly managed Mr. Hughes, who left the WWF after a few months. Wippleman was also the manager of Adam Bomb from October 1993 until June 1994, when Bomb turned face, and feuded with Kwang, who was also being managed by Wippleman. Wippleman also managed Well Dunn, who faced the Rock 'n' Roll Express in the latter's WWF debut on October 10, 1993.
Since debuting in the WWF, Wippleman was always at odds with ring announcer Howard Finkel, whom Wippleman believed introduced him in a condescending manner. At WrestleMania X, Wippleman tore up Finkel's tuxedo, and Finkel shoved him to the mat. The feud culminated in a tuxedo match on the January 9, 1995 edition of Monday Night Raw, which Finkel won.
Wippleman's next high-profile storyline was later in 1995, when he managed his on-screen girlfriend Bertha Faye. Faye, with Wippleman in her corner, won the WWF Women's Championship by defeating Alundra Blayze at SummerSlam 1995. After losing the WWF Women's Championship in late 1995, Faye was dropped from the WWF roster and Wippleman disappeared from television.
By spring 1996, Wippleman began making appearances on WWF Superstars, critiquing the referees during the matches in preparation to make a full report to WWF President Gorilla Monsoon about the apparent lack of consistency amongst the officials. Monsoon rewarded Wippleman for his efforts by making him an official referee. One of Wippleman's last appearances as a regular WWF referee during this time came on the March 10, 1997 episode of Raw when Chyna gorilla pressed him into a group of referees. On the May 19, 1997 episode of Raw, Wippleman appeared in a backstage segment with Stone Cold Steve Austin telling Wippleman that he was going to be his tag team partner with Wippleman responding that he was scared. Wippleman also appeared as "Handsome Harvey," introducing D-Generation X on Raw on November 24, 1997.
In June 1999, after another period of absence from television broadcasts, Wippleman resurfaced on the June 13 episode of Sunday Night Heat as a referee in a match between then-Intercontinental Champion Jeff Jarrett and Test. Test won the match after outside interference, thus being named the new champion, but he was persuaded by Jarrett's valet Debra to overturn the result and return the belt. He also served as a scab official during the WWF referee strike in September 1999, including at the Unforgiven pay-per-view, again refereeing a match with Jarrett defending the Intercontinental title against Chyna.
On January 31, 2000, Wippleman won the WWF Women's Championship from The Kat while he was in a disguise and used the name "Hervina" in a "Lumberjill Snow Bunny" match, which took place in a snow-filled pool surrounded by female wrestlers who kept the competitors from leaving the pool. The win made him the first male to hold the Women's Championship. He lost the title the following day to Jacqueline in a match that lasted under a minute, thus ending the shortest reign in the title's history. Through the remainder of 2000, Wippleman appeared in backstage and non-match segments of the WWF's television programming, including a segment on the April 23, 2000 episode of Sunday Night Heat where he appeared dressed up as a rabbit as part of a segment with Al Snow and Steve Blackman.
At WrestleMania X-Seven on April 1, 2001, Wippleman managed Kamala during the gimmick battle royal.
At the point the Invasion storyline began in 2001, he had disappeared from WWF programming, and was then working as a road agent for the company.
On November 15, 2010, for WWE's "Old School" episode of Raw, Wippleman returned to WWE, managing the Brooklyn Brawler in a squash loss to Ezekiel Jackson.
On January 22, 2018, Harvey made a brief backstage appearance during Raw 25 Years.