He spent time in the youth teams at Bradford City and Silsden before making his first-team debut for Guiseley in December 2013.

He was named Torquay's Player of the Year for the 2019–20 season but left the club shortly after their defeat in the 2021 National League play-off final.

[6] On 3 December 2013, Whitfield made his debut for Guiseley in a 2–1 victory over Selby Town in the quarter-finals of the West Riding County Cup.

[23] He received the first booking of his career on 1 April, when he was dismissed for an elbow on Tom Miller in a 2–0 defeat to Carlisle United at Huish Park.

[27] He maintained a first-team place under Michael Brown's stewardship, and held on to his place under new manager Neil Aspin, and his well-taken volley secured Aspin his first win as "Valiants" manager in a 3–1 victory over Cheltenham Town at Vale Park on 14 October; the goal was later shortlisted for the League Two goal of the month award.

"[38] He was in and out of the first-team as he struggled for consistency under both Aspin and new manager John Askey, and ended the 2018–19 season on the transfer-list after he scored four goals in 33 appearances.

[45] He won the club's Player of the Year award and was described as "a great asset to the squad" by manager Gary Johnson.

[46] He scored six goals from 33 appearances in the 2020–21 season, but ended the campaign injured and was not in the matchday squad for the play-off final defeat to Hartlepool United.

[47][52] On 21 July 2022, Whitfield signed for League Two club Barrow on a two-year deal; he joined on a free transfer, with Stockport retaining a sell-on fee.

[53][54] He was nominated for League Two's Player of the Month award for August after starting his time at Holker Street with four assists and one "superb solo" goal against Bradford City.

Whitfield adapted well to the new role, winning a nomination for the EFL League Two Player of the Month Award after he scored four goals in December.

[61][62] During his time at Holker Street, Whitfield became widely known amongst supporters as 'Tricky Ben', a nickname derived from a chant, reflecting his speed and agility on the field.