Born in Nassau, Holowesko won the Bahamas Cycling Federation's junior National Time Trial in the open all-ages category at the age of 13, in 2014, riding on a Cervélo S2.[4][5] He won the time trials again in 2015, and came in second in the road race.[6] In the Junior Tour of Ireland in 2016, riding for the US based Hot Tubes, Holowesko held the white jersey for two consecutive days.[7]
He is a two-time USA Junior National Time Trial Champion.[8] He also won the Bahamian National Road Race Championships in 2018,[9] and the Bahamas Pro National Championship Time Trials in 2014, 2015[10] and 2017.[11]
Holowesko signed to ride with Hagens Berman Axeon for the 2019 season at the age of 18, which made him the youngest member of the team.[1] Prior to signing with Hagens Berman Axeon, he rode for Hot Tubes Development Cycling Team.[12]
