Brentford 2020–2021 After beginning his career in the
Heart of Midlothian and
Aston Villa academies, Pressley transferred to the
B team at
Championship club
Brentford on 29 January 2020. During what remained of the
COVID-19-affected 2019–20 season, he scored three goals in six appearances. As a result of the
EFL permitting 9
substitutes to be named in matchday squads partway through the
2020–21 season, Pressley was promoted onto the first team substitutes' bench and was named in 15 matchday squads between November 2020 and February 2021. He made three substitute appearances during the period, but was not involved in Brentford's promotion-winning
playoff campaign at the end of the season. In May 2021, he signed a new two-year contract, with a one-year option.
2021–22 season and AFC Wimbledon loan In July 2021, Pressley joined
League One club
AFC Wimbledon on
loan for the duration of the
2021–22 season. Prior to being sidelined for 9 weeks with a hamstring injury suffered in a mid-December 2021 training match, he had made 25 appearances and scored four goals. Pressley was named in Brentford B's 2022
Atlantic Cup squad and made one appearance at the tournament. Following his return to the AFC Wimbledon squad in late February 2022, Pressley made two substitute appearances before suffering a reoccurrence of the injury,
2022–2023 and Accrington Stanley loan Pressley returned to match play with the B team in mid-November 2022 and on 4 January 2023, On his second appearance, Pressley's two goals and performance in a
EFL Trophy quarter-final
penalty shoot-out win over
Lincoln City saw him win the competition's Player of the Round award. He ended his spell with 27 appearances and eight goals, The one-year option on Pressley's Brentford contract was exercised at the end of the 2022–23 season. During the
2023–24 pre-season, he was included in the first team's
2023 Premier League Summer Series squad and made a substitute appearance in the opening match versus
Fulham. On 2 August 2023, Pressley departed the club. During a
2023–24 season in which he missed three months due to injury, he made 25 appearances and scored four goals. He returned to match play on 19 October 2024 and made seven appearances before joining League Two club
Barrow on loan for the remainder of the season on 9 January 2025. Pressley ended the
2024–25 season with four goals in 21 appearances and was retained by Stevenage for
2025–26. Pressley transferred away from the club in June 2025 and ended his two seasons at
Broadhall Way with 32 appearances and four goals. He made 41 appearances and scored seven goals during a mid-table
2025–26 season. == International career ==