2. “The British Bulldog” Davey Boy Smith
Davey Boy beat The Undertaker twice during an UK Tour, on April 30, 1991 and May 01, 1991, both times via DQ. It’s not known exactly what has caused the Disqualifictions, but with The British Bulldog bein a beloved Babyface at that time, even more so in his home country of England, it’s most likely a result of The Undertaker being caught cheating and breaking the rules.
Later that Year, The Undertaker got his win back by defeating The British Bulldog in a match for Taker’s WWF Championship.
On the May 27, 1996 epsidode of WWF Mondy night RAW, The Undertaker lost to Davey Boy via Count Out.
3. “The Macho Man” Randy Savage
On August 02, 1991, a (kayfabe) retired “Macho Man” Randy Savage beat the Undertaker in the Main Event of an untelevised Pittsburgh, Pennsylvania House Show Event, held in the Pittsburgh Civic Arena.
Just 1 day earlier in Moncton – New Brunswick, Canada, they main evented aswell, only the result was different with The Undertaker going over.
