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 Dr. gimmick and went by just his original name "Harvey Wippleman". Wippleman continued to feud with the Undertaker and brought a new wrestler to the WWF, the nearly eight-foot-tall Giant González, who interfered in the 1993 Royal Rumble and eliminated the Undertaker. Gonzalez and the Undertaker wrestled at WrestleMania IX, where Gonzalez knocked Undertaker unconscious with a ether-soaked rag. The feud culminated in a Rest in Peace match at SummerSlam, which Undertaker won. During this period, Wippleman also briefly managed Mr. Hughes, who also feuded with the Undertaker and took possession of the Undertaker's urn. Hughes however, left the WWF after only being with the company for a few months.
Wippleman was also the manager of Adam Bomb from October 1993 until June 1994 when Bomb turned face.
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, who responded by shoving Harvey to the mat. The feud culminated in a Tuxedo match on the January 5, 1995 edition of Monday Night RAW. 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 the WWF Women's Championship was abandoned 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. Wippelman 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 PPV, 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, a match that took place in a snow filled pool surrounded by female wrestlers whose purpose was to keep 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 (but broadcast on February 3) 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. By the time the Invasion storyline began in 2001, he had disappeared from WWF programming once again and transitioned to a road agent role with the company.
At WrestleMania X-Seven on April 1, 2001, Wippleman managed Kamala during the gimmick battle royal.