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 appearances 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