Punishment: 2-game suspension
A notoriously dirty player, Claude Lemieux will forever be remembered as one of the least-liked NHL players of all-time. Perhaps his most famous incident was this one with Kris Draper, which occurred during a hotly-contested playoff series between the Red Wings and Avalanche that touched off one of hockey's biggest rivalries of the late-90s. Lemieux's check sent Draper face-first into the boards, breaking his jaw, nose, and cheekbone while also causing a concussion. Despite these extensive injuries that forced Draper immediately into facial reconstructive surgery, Lemieux somehow escaped with only a two game suspension.
30. Claude Lemieux rearranges Kris Draper's face on the boards with hit from behind.