He first joined Huddersfield Town's academy in the late-2000s, after a spell at the Manchester United Academy and signed his first professional contract at the club. In October 2010, he travelled with the Town squad for their League One match against Plymouth Argyle, and a few days later, he was named on the bench in their FA Cup match against Cambridge United. Ahead of the 2011–12 season, Crooks was among other youth players to be expected to be loaned out to gain first team experience. Nevertheless, in November, Crooks signed his first professional contract with the club, until 2014. It was announced on 9 February 2012 that Crooks was nominated for League One Apprentice of the Year., however, he ultimately lost it out to Charlton Athletic's Jordan Cousins. In March 2012, it announced that Crooks would be joining Halifax Town on a one-month loan. While at Halifax Town, Crooks scored his first professional goal in a 4–0 win over Histon. That soon earned him a loan extension until the end of the season. Crooks was even allowed to play for the club's promotion push. For the following season, 2012–13, Crooks was given number 36 shirt, however, he failed to make an appearance for the first-team. On 7 December 2012, Crooks, along with James Burke, joined Radcliffe Borough on loan until mid-January. Crooks made an impressive display at the club, including when he scored a brace against Clitheroe. Two days later, Crooks made his return to Huddersfield Town. After returning to Huddersfield Town, Crooks remained playing in the club's reserve. However, Crooks sustained an ankle injury during a development match in early October. Following a surgery, it was announced that Crooks would be on the sideline for two months. Following his return in mid-February, Crooks was praised for his return from injury and playing as a central defence. At the end of the 2013–14 season, Crooks was offered a new contract by the club. Ahead of the 2014–15 season, Crooks switched number shirt from thirty-six to twenty-two after Ed Wilczynski took over Crook's first number and made an impressive display as a centre back in the pre-season friendly that convinced Mark Robins to use him. After years playing at the reserve and be loaned out twice at the time, Crooks finally made his first team début at centre back for the Terriers in the 4–0 defeat by A.F.C. Bournemouth on 9 August 2014 in the opening game of the season. The loss, however, was to be Robins last game as a manager of Huddersfield Town, as he was sacked the next day Newspaper Huddersfield Daily Examiner urged the club's supporters to give Crooks time to make up his mistake after receiving criticism during the match, including the first goal. He did not make another appearance for Huddersfield that season and joined Hartlepool United on a month's emergency loan on 21 October 2014 as defensive cover. After making three appearance for the club, it announced that Crooks would make a return to the club following an expiry of a month loan with Hartlepool United. Three days after returning from his loan spell, he was sent on loan to fellow League Two side Accrington Stanley until 3 January. On 2 February 2015, Crooks left Huddersfield Town after having his contract terminated by mutual consent.
Accrington Stanley
Three weeks later, Crooks returned to Accrington Stanley signing an 18-month contract on 24 February 2015. After a strong start to the 2015–16 season which saw him score an extra time equaliser against Hull City in the Football League Cup and a 90th-minute equaliser against Notts County in League Two, Accrington manager John Coleman tipped Crooks to have a big future in the game. In January 2016 it was announced that Scottish club Rangers had approached Crooks and teammate Josh Windass with a view to them signing pre-contract agreements. The talks angered the Accrington chairman Andy Holt as Rangers were only required to pay a nominal fee to complete the transfers for both players under FIFA regulations. The following day both players agreed pre-contracts with Rangers to join the club in the summer of 2016.
Rangers
Crooks officially joined Rangers on 1 July 2016, signing a four-year contract alongside fellow Accrington player Josh Windass. Both players had already been training with the club prior to completing their transfers after Rangers agreed a compensation fee with Accrington, reported to be around £60,000 per player. He missed the start of 2016–17 season due to an ankle ligament injury but returned to playing in an under-20 match against St Mirren in late August. Crooks made his first-team debut against Queen of the South in a Scottish League Cup match, appearing as a 72nd-minute substitute on 20 September 2016. However, Crooks has only made a few sporadic appearances for the club thereafter and this led many to criticise then Rangers manager Mark Warburton's transfer policy.
Northampton Town
Crooks officially joined the English League One side on 18 July 2017 for an undisclosed transfer fee after only three appearances with Rangers FC. On 9 September 2017, Crooks scored his first competitive goal for the Cobblers after 21 seconds of the game against Doncaster Rovers, this was the quickest goal ever scored in a competitive match at Sixfields Stadium.
Rotherham United
On 11 January 2019, Crooks joined EFL Championship side Rotherham United for an undisclosed fee, signing a three-and-a-half year contract.
