Bob Hollys injury is one of the more controversial on this list. Back in September 2002, Holly was facing an inexperienced Brock Lesnar, when a botched powerbomb saw him dropped unceremoniously on his headcrushing his neck in the process. The debate that rages on centres around whose fault it actually was, with many claiming that Holly was sandbagging Lesnar in some sort of initiation for the newbie. The facts remain unclear though, with Holly countering that argument by claiming that if Brock had really wanted to powerbomb him, then no amount of sandbagging would have nullified the future UFC stars strength. One things for sure though; Holly had ruptured a disk in his neck and would require a surgery that ultimately kept him out of action for 13 months. Upon his return he looked to exact revenge on the man who had sentenced him to the side lines, but in the end came up short in his quest. Nonetheless, to have returned from such a debilitating injury was no small feat for a man of nearly 40 years old.