Gregor Gillespie entered the Octagon to face Kevin Lee at UFC 244 as an undefeated prospect with a decorated background in amateur wrestling. Lee was a step up in competition for Gillespie, and the fight turned out to be a step too far for the New York native fighting in front of a hometown crowd at Madison Square Garden.

Lee (18-5) and Gillespie (13-1) traded hard shots of the feet as the fight got underway. Lee's primary job was to make it hard for Gillespie to close distance where he could take over the fight with his wrestling skills. He did that with a stiff jab but was taking shots in return. That is, until Lee caught Gillespie with a massive left head kick that sent the wrestler crashing backward into the cage, unconscious and bouncing to the canvas.

The referee stopped the fight as Gillespie was unconscious at the 2:47 mark of Round 1, snapping Lee's two-fight losing skid and handing Gillespie the first loss of his career. Prior to the loss, Gillespie was 6-0 in the UFC with his five most recent fights ending via stoppage.

"I needed to make [a statement] tonight." Lee said after his victory. "My back was against the wall. I'm coming out here facing the most decorated wrestler in the division and I wanted to put on a show."

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