booker t - wrestlemania 19 , beat him in the World Title match, former WCW star getting his first real push in WWE, a win over Triple H would have been huge instead he loses not to mention it takes HHH over 20 seconds to pin him after hitting a pedigree, racist angle etc.....don't forget Summer Slam 2007 when Booker T loses to HHH again, shortly there after goes to TNA....
Jericho - Beats him at Wrestlemania X-8 , takes the undisputed title off him, Jericho was hot at this time
CM Punk - Night of Champions 2011 ... CM Punk has the summer of punk which sees him beat john cena clean at money in the bank is the hottest thing in wrestling until he runs into night of champions
Goldberg - destroys goldberg at Summer Slam 2003 in the elimination chamber match, beats him in a series of matches in late 2003
kurt angle - beat angle several times during summer 2000 when embroiled in love triangle angle with stephanie, "winning" the feud
scott steiner - beats him in two title defenses, royal rumble 2003 and no way out 2003 after this steiner is a mid card talent, this man at one point was main eventer in wcw
sting - arguably the greatest wcw performer of all time , loses his debut wwe match at wrestlemania 31 to HHH, effectively burying him and spitting in the face of one of the most untouchable legacies in professional wrestling