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Winn would go on to earn Fight of the Night honors in his fight with Spicely, adding even more hype behind the American Kickboxing Academy product. The thrill of a victory in his debut led Winn to make the walk to the Octagon a second time to face Darren Stewart at UFC Boston in October.
The showdown with “The Dentist” was a closely contested battle, with Winn relying heavily on his wrestling to control the action. Yet after the first round, Winn found himself struggling, both physically and mentally. He would go on to lose the bout by split decision.
Winn believes that despite the loss, he proved something to himself and that the version of Deron Winn the world will see going forward will be a completely different fighter.
“Coming off a loss it was kind of shaky,” he said. “I didn’t really know how to handle it because it was my first loss in MMA, but as a wrestler and true grinder at heart, I took a lot of these values and training ideas that I’ve always had and then I ramped it up. I’ve always had heart, but I think it affirmed to me that I have maybe an even bigger heart than I ever thought that I had because I had a bunch of crazy and negative thoughts when I was out there. If you understood how tired and out of it I was compared to how I looked, you’d be blown away. It changed a lot in me and I’m more confident than ever now.”
And after that loss, Roufusport’s Meerschaert reached back out to rekindle the sparring on Twitter. It didn’t take long for Winn to accept Meerschaert’s challenge and, just like that, the Twitter fingers turned into a bad blood battle on this weekend’s UFC 248 card.