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Fentrell Cypress was an On3 Consensus three-star recruit coming out of Rock Hill (South Carolina) Northwestern High School in the 2019 recruiting class. He was originally the No. 14 recruit coming out of the state and he signed with UVA over interest from a number of ACC and SEC teams. In 2022, Cypress notched 29 tackles and a fumble recovery. He led the ACC with 14 pass breakups and passes defended per game. The 1.56 passes defended per game were the fourth-most in the country. Cypress started all nine of the games in which he appeared and was credited with 39 tackles. He was named second-team All-ACC for his efforts. Since recording two tackles in 2020, the 6-foot-0, 170-pound corner increased his role on the Virginia defense. In 2021, he made six stars with 17 tackles, including a half-sack, plus an interception.

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