Cruickshank faced Mike Rio on January 25, 2014 at UFC on Fox 10. He won the fight by wheel kick to the face and punches at 4:56 of the second round.
Cruickshank faced Erik Koch on May 10, 2014 at UFC Fight Night 40. Cruickshank, a significant betting underdog, won the fight via TKO due to a kick and punches in the first round.
Cruickshank faced Jorge Masvidal on July 26, 2014 at UFC on Fox 12. He lost the fight via unanimous decision.
Cruickshank faced Anthony Njokuani on October 4, 2014 at UFC Fight Night: MacDonald vs. Saffiedine. He won the fight by unanimous decision.
Cruickshank faced K.J. Noons on December 12, 2014 at The Ultimate Fighter 20 Finale. After a back-and-forth first round, the fight was stopped in the second round when Cruickshank received a second inadvertent eye poke from Noons and was unable to continue. Because they had not reached the third round, the fight was declared a No Contest.