Early career Cheek spent time in the youth team at
Port Vale, though he did not enjoy his time at
Vale Park. He moved to
Colchester following his parents' separation, and spent a year on the east coast of Australia at age 18. He re-joined Stanway for a second spell, where he scored 34 goals in 60 games in all competitions, before signing for
Heybridge Swifts in May 2012.
Chelmsford City In January 2014, following 13 goals in 20
Isthmian League Division One North appearances for Heybridge Swifts during the opening months of the
2013–14 season, Cheek signed for
Conference South club
Chelmsford City. Cheek's arrival at the club followed former Heybridge manager Mark Hawkes, who had joined Chelmsford in November 2013. On 21 January 2014, in his second game for the club, Cheek scored his first Chelmsford goal, in a 3–1 win away to
Concord Rangers. Cheek finished the
2013–14 season with 12 goals from 20 appearances, On 28 December 2014, Cheek recorded his second four-goal haul for Chelmsford in a 5–3 win away over
Staines Town. Despite only scoring one goal in his final 13 appearances for Chelmsford, Cheek scored 23 goals in 46 appearances in all competitions for the club during the
2014–15 season.
Braintree Town On 23 May 2015, Cheek signed for
National League club
Braintree Town. Upon signing, Braintree boss
Danny Cowley said "
Cheek was the best all-round forward in the Conference South last year". Braintree qualified for the play-offs at the end of the
2015–16 season, which Cowley described as "nothing short of a miracle". They lost out to
Grimsby Town in the semi-finals. After scoring 15 league goals in his debut season for the club, Cheek signed a new one-year deal with Braintree in June. Ahead of the
2016–17 season, after playing as a lone striker in the previous campaign, Cheek's role at
Cressing Road changed, following the appointment of
Jamie Day and the signings of
Lee Barnard and
Jack Midson. Day was sacked in September, and was replaced by
Hakan Hayrettin, who demanded his players to work hard in every match. Cheek scored a hat-trick in a 5–2 victory at
East Thurrock United in the
FA Trophy. He scored 19 goals in 44 league appearances as Braintree were relegated back to the National League South. He was the division's fourth-highest scorer and also claimed eight assists. at which point he became a fully professional footballer. He suffered a knee injury, which he recovered from. He scored 13 goals in 36 games across the
2017–18 campaign, He started four of the club's first 20 league games under
Daryl McMahon, before gaining starts after new manager
Garry Hill switched to a front-two formation with him and
Danny Kedwell. Cheek was named as National League Player of the Month for December after scoring eight goals in 10 games. He was named on the National League Team of the Week after scoring a brace in a 4–2 win over Wrexham at
Stonebridge Road on 30 March. He scored 16 goals in 39 league games during the
2018–19 campaign, Off-field financial issues meant that Ebbsfleet players were paid late, though the club denied accusations of deceiving their players. He remained under contract, though he was moved on to help ease the club's financial pressures. Upon his departure, Cheek said to the local press "''This season has definitely taught me a lot, on and off the field. I've met some great players and I've learned that, as a team, we can do more even if off-field issues are a problem. It's the best group of players I've played with in all honesty, characters and talent-wise. It's just a shame the way it's ended''."
Bromley On 10 May 2019, Cheek signed for National League club
Bromley. Manager
Neil Smith said that "
to get someone of his quality into our side for next season is massive for us". Cheek scored on his home debut for Bromley against his former club Ebbsfleet in a 3–1 win on 6 August. He scored 15 times in 45 appearances in the
2019–20 campaign. Following the
2020–21 season, Cheek won the Golden Boot award after scoring 21 league goals for Bromley in the National League, as well as a further four in cup competitions. On 22 May 2022, Cheek scored the only goal in the
FA Trophy final against
Wrexham at
Wembley Stadium. having scored 17 goals in 42 league games across the
2021–22 campaign. On 5 May 2024, he scored twice at Wembley in the
play-off final. Bromley drew the game 2–2 and won 4–3 on penalties against
Solihull Moors. Cheek also scored his penalty in the shootout. The win meant that Bromley had secured promotion to the
English Football League for the first time in the club's history. Overall, he scored 26 goals in 53 appearances across the
2023–24 season. He also won 11 aerial duels during the game, earning himself the fifth-highest rating in League Two that weekend. He was nominated for the
League Two Player of the Month award after scoring three of Bromley's four goals in September. He was named League Two Player of the Week afer scoring the only goal of the game against
Fleetwood Town on 15 February, also winning 12 aerial duels during the match. He was nominated again as that month's League Two Player of the Month following three goals and two assists. On 27 April, he was named League Two Player of the Season. He was also the division's Golden Boot with 25 goals, six more than any other player, and claimed seven assists to take him to 32 goal involvements. He was also named as PFA League Two Players' Player of the Year. Cheek was reported to have handed in a transfer request in August 2025, though manager
Andy Woodman insisted that Cheek was one year into a three-year contract and was going nowhere "unless
Liverpool want to take him instead of
Isak". The club rejected multiple bids from
Stevenage. He continued his good form despite such speculation, being the top performer of gameweek seven by scoring and assisting in a 2–2 draw with
Gillingham. On 29 December, he scored a hat-trick in a 3–1 win at
Crawley Town. By this time he had already established himself as Bromley's highest goalscorer in the modern era, not counting amateur player George Brown's tally of 570 goals set between 1938 and 1961, but surpassing Butch Dunn's tally of 132 goals set between 1978 and 1982. On 10 January, he scored both goals in a 2–0 victory at
Tranmere Rovers, also winning 14 aerial duels as he secured consecutive EFL Team of the Week inclusions. He picked up another brace on 28 February, converting two penalties in a 2–1 win over
Accrington Stanley, also making two key passes and a header against the crossbar. ==International career==