Cruikshank majored in general studies at Arizona after playing at Citrus College for the 2013 and 2014 seasons.[2] He was named first-team all-state.[3]
As a redshirt junior in 2016, he played cornerback, tying the team lead in interceptions with two, finishing fourth in total tackles with 60 and second in pass breakups with seven.[2]
As a redshirt senior in 2017, he switched to safety, ranking fifth on the team with 75 total tackles, tying for second in interceptions with three and ranking third in pass breakups with five.[2]
Cruikshank was drafted by the Tennessee Titans in the fifth round (152nd overall) of the 2018 NFL draft.[6] On May 11, 2018, he signed a four-year contract worth $2,747,892 with $287,892 in guarantees.[7]
“We take special teams very seriously over here,” Cruikshank said following the game. “Everybody takes advantage of their opportunities and I rose to the occasion (Sunday) and made the best of it.”[10]
2020 season
On September 6, 2020, Cruikshank was placed on injured reserve.[11] He was activated on October 24, 2020.[12] In week 7 against the Pittsburgh Steelers, Cruikshank recorded his first career interception off a pass thrown by Ben Roethlisberger during the 27–24 loss.[13] He was placed back on injured reserve on November 11, ending his season.[14]
2021 season
Cruikshank was placed on injured reserve after missing a week of practice with a knee injury on November 13, 2021.[15] He was activated on December 11.[16]
Chicago Bears
On March 31, 2022, Cruikshank signed with the Chicago Bears.[17] He was placed on injured reserve on November 30.[18]
New York Jets
On July 20, 2023, Cruikshank signed with the New York Jets.[19] He was released on August 25.[20]
On May 13, 2024, Cruikshank signed with the Atlanta Falcons.[23] He was released on August 27, and re-signed to the practice squad.[24][25] Cruikshank was released on October 1 and re-signed to the practice squad two weeks later.[26][27] He was released again on December 9.[28]