On May 21, 2010, Strikeforce brought its Challenger Series to Portland, Oregon. While Challenger Series events were designed to bring exposure to the promotion’s up-and-coming talent, they also typically featured at least one bout with more established fighters at the top of the card. Strikeforce Challengers 8 was no exception, headlined by middleweight pioneer, Olympic silver medalist, and general Oregonian favorite son Matt Lindland.

While Lindland’s legacy—which started in the 90s and saw him challenge for an Ultimate Fighting Championship title—was as unimpeachable as his bars on the immortal International Fight League anthem, he was definitely in need of a win at the time. “The Law” had lost his last two fights via first-round stoppage, albeit to high-level fighters in Vitor Belfort and Ronaldo Souza.

As it turned out, Lindland notched that win and then some, as he worked over Kevin Casey in increasingly dominant fashion for over two rounds before dispatching him with ground-and-pound in the third. He looked impressive doing so, fearlessly grounding the Rickson Gracie black belt, advancing to dominant positions on the ground and even snaring a tiring Casey in a crucifix at the end of the second round. It would be the last win of Lindland’s fight career: After losing his next two fights—once again in the first round and once again at the hands of top-notch competition in the form of Robbie Lawler and Mamed Khalidov—Lindland hung it up. Since then, he has remained busy, working with USA Wrestling, appearing in television and films, and hopefully working on his debut album as a solo MC.



Of course, Lindland was not the only MMA hip-hop royalty to fight that night at Challengers 8. Still a few years away from truly hitting his stride as a fighter/rapper, the 5-0 Tyron Woodley took on Portland native Nathan Coy in the co-main event. Former University of Missouri wrestling star Woodley faced the sternest test of his young career in Coy, himself a former NCAA All-American. While Challengers 8 marked Lindland’s final win, it also came close to being Woodley’s first loss, as he prevailed in a split decision that had the partisan crowd in Portland booing heavily.

Woodley would go on to fight for the vacant Strikeforce welterweight title, losing to Nate Marquardt, before jumping to the UFC, where he would win the belt with a stunning knockout of Robbie Lawler at UFC 201. He then defended the belt four times before losing it to current champ Kamaru Usman last year.