He signed with Virginia Tech out of high school and played in 4 games in 2017 before transferring to Central Michigan where he played from 2019 to 2021.[3] He earned MAC Special Teams Player of the Year honors in 2021 for his kick returning and was a first team All-MAC wide receiver.[4]
On April 30, 2022, Pimpleton was signed by the Detroit Lions after going undrafted.[6] On August 29, Pimpleton was waived by the Lions.[7][8][9]
New York Giants
On September 1, 2022, Pimpleton was signed to the New York Giants practice squad.[10] He signed a reserve/future contract on January 22, 2023.[11] He was waived on August 29, 2023.[12]
Ottawa Redblacks
Pimpleton signed with the Ottawa Redblacks on January 23, 2024.[13] Following training camp in 2024, he began the season on the injured list, but soon after made his CFL debut in week 6 on July 14, 2024, against the Edmonton Elks.[14] In that game, Pimpleton scored his first career touchdown, on a 70-yard touchdown catch thrown by Dru Brown, and recorded an 100-yard game.[14]