On 14 January 2019, Crookes joined struggling League Two side Port Vale on loan for the remainder of the 2018–19 season.[17][18] Manager Neil Aspin state that "A natural left-footer in the defence is something we've not had and he'll compete for a place".[19] He made his debut in the English Football League in a 1–0 win at Crawley Town on 19 January.[20] He maintained his first-team place under new manager John Askey, impressing both playing on the left of a back three and at left-back in a back four.[21] Assistant manager Dave Kevan said that Crookes had good character and that the management team would monitor his availability in the summer.[22] Nottingham Forest released Crookes on 13 May 2019.[23] However, his agent Phil Sproson revealed that he had received contract offers from Vale and another, unnamed club.[24] He signed a two-year deal with Port Vale on 31 May.[25]
He began the 2019–20 season playing at left-back and said that he had been studying Liverpool full-back Andrew Robertson to improve his performance in the role.[26] He maintained his first-team place until a "freakish training accident" saw him sidelined in late-October.[27] He returned to training after a four-month layoff, but was unable to add to his 17 starts before the season was ended early due to the COVID-19 pandemic in England.[28][29]
He struggled for playing time at the start of the 2020–21 season as he was behind centre-backs Nathan Smith, Leon Legge and Shaun Brisley in the pecking order, though impressed the management after filling in at left-back in the absence of Cristian Montaño and David Fitzpatrick.[30] He scored his first goal in professional football on 30 January, in a 5–1 home win over Southend United.[31] He started new manager Darrell Clarke's first two games in charge, playing left-back in a 4–4–2 and then left-sided centre-back in a 3–5–2 formation.[32] However, he was one of 15 players released at the end of the season.[33]
Grimsby Town
He signed a one-year contract with National League club Grimsby Town on 9 July 2021; manager Paul Hurst said he had been aware of Crookes for some time and that former manager Clarke had spoken well of him.[34][35] He played 24 league games in the 2021–22 campaign, helping the "Mariners" to qualify for the play-offs with a sixth-place finish.[36] Grimsby secured promotion with victory in the play-off final. However, Crookes was not in the matchday squad at London Stadium.[37] On 11 June, the club announced their retained list and confirmed that Crookes would be released upon the expiry of his contract at the end of the month.[38]
York City
On 30 June 2022, Crookes joined newly promoted National League club York City, alongside Grimsby teammate Scott Burgess, both of whom had played under York manager John Askey at Port Vale.[39] He recovered from an injury early in the season and signed a two-and-a-half-year contract in January 2023.[40] He was named in the National League Team of the Week on 9 April following good performances against Chesterfield and Barnet.[41] He made 23 appearances in the 2023–24 season,[36] after having missed the final six weeks with a hamstring injury.[42] He suffered a quad injury in August 2024 that kept him sidelined for six weeks; manager Adam Hinshelwood commented that he would be a "big miss".[43]
Playing style
Crookes has been described as "a left-sided defender equally comfortable playing left-sided centre back or at left back [who] can also play as a defensive midfielder if required".[5]