Insanity Pro Wrestling Legally Insane 2008 took place in Indianapolis, Indiana.
- Numbers in parentheses indicate the length of the match.
- (c) refers to the champion(s) heading into the match.
- The Clash (Brian Bender & Ernie Ballz) defeat Jake Crist & Vincent Nothing in a IPW Tag Team Title Tournament First Round Match
- The Naptown Dragons (Dustin Lee & Scotty Vortekz) defeat Hillbilly Jed & Osyris in a IPW Tag Team Title Tournament First Round Match
- Drake Younger (c) defeats Carlton Kaz in a No Holds Barred IPW Grand Championship / MPW Heavyweight Championship Match