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#4 Monday Night Raw (June 21, 1999) - WWF Championship
Their encounter on Monday Night Raw in June 1999, came amidst The Undertaker's third reign as WWF Champion.
Triple H was finally starting to gain traction with the fan-base as a legitimate title threat and so the pair clashed in what was their first significant match with each other.
It was a typical Attitude Era brawl wherein the participants fought all over ringside.
It was an entertaining match while it lasted but in truth, this encounter was just a set up for Undertaker's title defence versus The Rock at King of the Ring six days later.
It was The Rock who caused the finish as he entered the ring and Rock Bottomed Undertaker to cause the DQ finish.
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