Ryan made his debut at Pride 10 against Tokimitsu Ishizawa and dismantled the Japanese wrestler in just over two minutes. Gracie lost the rematch due to injury, but Ishizawa was getting the best of him in that bout. Tokimitsu took the bout very seriously and stated he would retire from MMA if he did not win. Ryan faced the then unstoppable Kazushi Sakuraba at Pride 12 and lost a decision. Some fans may remember Ryan came to ring covered in blue tape and required a special one-round bout.
In his return to action at Pride 22, Ryan dominated Japanese striker Shungo Oyama and stopped him with a vicious armbar that looked like it almost made Oyama pass out. Ryan was back on top. He knocked out Kazuhiro Hamanaka with a kick at Pride Bushido 1 and won a very questionable decision over Ikuhisa Minowa at Pride Bushido 3 (ok, plain and simple, he lost).
MY PICK: Before I answer, the question has to be asked: What is the point of this? Are we trying to tie this back to the little known closed-door dojo bout between Anjo and Rickson Gracie way back before to Pride 1? Sorry to dip my toe in your champagne fountain guys, but most people dont even know enough about that fight to reference it. Those that do dont care. Im going with Gracie. If he ever hopes to fight again he cant afford to lose to this guy. Gracie by TKO in the first round.