Gillingham Born in
Gravesend, Kent, Hessenthaler began his career with
Chelsea as an Under-8 in their
youth system and was 15 when Chelsea released him after seven years with the club. He signed his first professional contract with
Gillingham in February 2013. In January 2013, Hessenthaler signed for
Merstham on loan. After loan spells with
non-League clubs
Lewes,
Tamworth and
Margate, he made his debut for Gillingham on 30 November 2013 as an 85th minute substitute in a 4–1 away league loss to
Rotherham United. On 7 February 2014, Hessenthaler signed a new long-term deal at Gillingham to keep him contracted until the end of the 2017–18 season. He scored his first goal for Gillingham in a 4–2 win at home to
Coventry City on 11 March 2014, with a 40-yard strike in the 90th minute. His goal against Coventry earned him Gillingham's 'Goal of the Season' award, whilst he also won the club's 'Young Player of the Year' award for the
2013–14 season.
Grimsby Town He was released by Gillingham at the end of the 2017–18 season and signed a two-year contract with
Grimsby Town on 25 June 2018. He scored his first goal for Grimsby in a 2–1
EFL Trophy win over
Notts County on 4 September 2018. On 28 January 2020, he suffered a punctured lung, a broken rib, and ligament damage across the shoulder and collarbone as a result of a challenge by
Simeon Jackson in the first minute of a 3–1 victory over
Stevenage.
Crawley Town Hessenthaler was released by Grimsby at the end of the
2019–20 season. On 1 September 2020, he signed for fellow
League Two side
Crawley Town. He scored his first goal for Crawley on 30 January 2021 in a 3–1 defeat against
Cambridge United. On 31 January 2023, Hessenthaler joined
National League club
Woking on loan until the end of the season.
Dagenham & Redbridge On 21 July 2023, Hessenthaler signed a two-year deal with
Dagenham & Redbridge.
Ebbsfleet United In June 2025, Hessenthaler joined
Ebbsfleet United following their relegation to the
National League South. ==Personal life==