7. Kazuo Takahashi (27 losses)
Takahashi would do a lot of his early bouts in Japan’s Pancrase organization and actually did pretty well for himself for a time. In 2006 he had a 28W-18L record and was fighting for Pride when he was matched up with Vitor Belfort. A free-from-drug-testing Belfort made short work of Takahashi, taking just 36 seconds to knock him out.
After that Takahashi was a mess. He only won 2 of his last 11 fights (with 1 draw) to finish with a career record of 30W-27L.