- His hardcore match with Al Snow at WWF In Your House: St. Valentine's Day Massacre in 1999. A good mix of technical moves, Garbage Wrestling, stiff shots and psychology throughout, culminating with an unlikely win by Holly who covered Snow in chicken wire to win the vacated title (the first of six such wins) and disband the "dreaded" J.O.B. Squad. Bonus points for the match ending up in the Mississippi River before it was all over.
- His feud with Brock Lesnar where he decimated a good part of the SmackDown! roster, choked out The Big Show with a chair, looking a legit beast as he did so. At least, it was pretty awesome until the WWE Championship match.
- 2006. WWECW. Hardcore Holly. Rob Van Dam. Table match. Holly suffers a major gash and finishes the match. Cue standing ovation. For the record, the match itself was pretty dam(n) good until that whole thing happened.
- Also in WWECW, Holly became the first wrestler to withstand CM Punk's Anaconda Vice, and soundly defeated him shortly thereafter, giving Punk his first loss in WWE.
- Winning the Tag Team Championship with Cody Rhodes at the 15th anniversary of Raw. Of course, that didn't really work out so well for Holly, in the end.
Awesome / Bob Holly