Randolph made his professional debut with the Gulf Coast Phillies, batting .302 with one home run and 24 RBIs over 53 games.[5] In 2016, he played with the Lakewood BlueClaws where he hit .274 with two home runs and 27 RBIs over 63 games.[6] Randolph spent 2017 with the Clearwater Threshers, slashing .250/.338/.402 with 13 home runs and 55 RBIs over 122 games,[7] and after the season, played in the Arizona Fall League for the Glendale Desert Dogs.[8] He spent 2018 with the Reading Fightin Phils, batting .241 with five home runs and forty RBIs over 118 games.[9] In 2019, he returned to play for Reading, hitting .247 with ten home runs and 44 RBIs over 102 games.[10] Randolph did not play in a game in 2020 due to the cancellation of the minor league season because of the COVID-19 pandemic.[11] In 2021, Randolph spent the majority of the season with the Triple-A Lehigh Valley IronPigs, also appearing in 5 games for the Phillies' rookie-level affiliate, slashing .235/.323/.386 in with 5 home runs and 20 RBI in 48 games for the team. On November 7, 2021, Randolph elected free agency.[12]
Chicago White Sox
On March 8, 2022, Randolph signed a minor league contract with the Chicago White Sox.[13] Randolph was assigned to the Double-A Birmingham Barons to begin the season. After struggling to a .118/.211/.117 with no home runs and 1 RBI in 11 games for Birmingham, he was released by the White Sox organization on May 3.[14]
On May 1, 2023, Randolph re-signed with the Cougars.[17] In 63 games for the club, he hit .279/.372/.430 with five home runs and 36 RBI. Randolph became a free agent at the end of the season.
On January 20, 2024, Randolph signed with the Dorados de Chihuahua of the Mexican League.[18] However, he was released prior to the start of the season on April 10.[19]
On May 2, 2024, Randolph re–signed with the Kane County Cougars of the American Association of Professional Baseball.[20] Randolph slashed .343/.447/.527 with 11 home runs and 58 RBI in 79 games, helping the Cougars win their third Championship in their franchise history. This was also Kane County's first Miles Wolff Cup Championship since joining the American Association in 2021, sweeping the Winnipeg Goldeyes. Randolph won the Series MVP after he went 6–for–12 with two RBI including a walk off hit in game 1 of the series.[21]