In September 2009 he signed with Conference Premier side Mansfield Town, where he was told by manager David Holdsworth that he would be sent out on loan and then come back and stake a claim for the first team.[6][7] He spent time on loan at Glapwell (where he scored six goals in a single match – a 7–1 rout against Willenhall Town) and Conference North side Harrogate Town.[8][9] Despite scoring on his Stags debut in a 2–1 win against Southport on 11 September 2010, Gregory was unable to establish himself in Holdsworth's plans.[10]
FC Halifax Town
In the spring of 2010 Gregory was loaned to FC Halifax Town for the remainder of the season as back-up for the run-in in the eventual Northern Premier League Division One North title winning campaign, Gregory scoring five goals in 10 appearances, mainly coming off the bench.[11] He rejoined Halifax permanently in December 2010, being the club's third top scorer behind Jamie Vardy and Danny Holland as Halifax claimed back-to-back titles and promotions.[12]
Gregory finished the 2011–12 campaign in the Conference North as the club's top scorer with 18 league goals although promotion was missed out after losing to Gainsborough Trinity in the play-offs.[11] He scored a further 20 goals in the 2012–13 campaign as the Shaymen obtained another promotion this time via the play-offs after defeating Guiseley and then Brackley Town.[11] On 30 June 2013 Gregory signed a new two-year deal with Halifax,[13] and finished 2013–14 with 29 league goals under his name, being the division's second top goalscorer, behind only Luton Town's Andre Gray. Halifax finished in 5th position, losing to Cambridge United in the play-offs.[14] During the January transfer window Gregory nearly moved to Crawley Town.[15] At the end of the campaign Gregory was attracting interest from Football League clubs with Championship side Millwall making a number of bids.[16]
Millwall
On 16 June 2014, Gregory signed a three-year contract with Championship Millwall after the club agreed a fee with Halifax.[17] He scored his first Football League goal on 30 September 2014 in a 3–1 home defeat against Birmingham City.[18] Gregory was a regular in the 2014–15 season as Millwall struggled in the second tier and with relegation an inevitability, manager Ian Holloway was sacked in March 2014 and replaced by Neil Harris.[19][20] Gregory scored a hat-trick in a 3–3 draw against Derby County on 25 April 2015 but it was in vain as Rotherham United defeated Reading to relegate Millwall to League One.[21][22] Gregory scored on the opening day of the 2015–16 season, in a 2–1 victory over Shrewsbury Town.[23] He scored four goals against Plymouth Argyle in the EFL Trophy on 10 November 2015.[24] Gregory scored 17 goals in the second half of the campaign bringing his total to 27 which helped the Lions reach the 2016 Football League One play-off final where they were beaten 3–1 by Barnsley.[25]
Gregory signed a contract extension with Millwall in September 2016.[26] Millwall were involved in a tense fight for a play-off place throughout the season, eventually securing their place with a 4–3 final day success over Bristol Rovers, with Gregory scoring twice.[27] Gregory scored in the 3–2 semi-final 2nd leg win over Scunthorpe United and assisted Steve Morison for the only goal against Bradford City in the final.[28][29] He was sent-off for the first time in his professional career against Queens Park Rangers on 12 September 2017, a decision which angered manager Neil Harris.[30][31] Gregory scored ten goals in 47 appearances in 2017–18 as Millwall had a fine return to the Championship narrowly missing out on a play-off spot by three points.[32] At the end of campaign, his contract was extended by Millwall for an extra year after the club exercised an option.[33] He played 50 times in the 2018–19 season, scoring 13 goals helping the side finish in 21st position and avoid relegation.[34] Gregory left the Den at the end of the season with him expressing his desire to move back up north.[35][36]
Stoke City
On 25 June 2019, Gregory joined Championship side Stoke City.[37][38] He made his debut on 3 August 2019 in a 2–1 defeat against Queens Park Rangers.[39] He scored his first goal for Stoke in a 3–2 defeat against Nottingham Forest on 27 September 2019.[40] Stoke made a poor start to the 2019–20 season failing to win any of their first ten fixtures and were rooted to the foot of the table by October.[41] Gregory suffered a bizarre injury at the beginning of November after he locked his knee whilst in bed.[42] He recovered quickly and scored a penalty against Barnsley on 9 November 2019 helping new manager Michael O'Neill record a 4–2 victory.[43] He scored in the final two matches of the 2019–20 against Brentford and Nottingham Forest which saw Stoke avoid relegation and finish in 15th position.[44][45]
On 1 February 2021 Gregory joined Derby County on loan for the remainder of the 2020–21 season.[46] He scored his first goal for Derby in a 2–1 win against Middlesbrough on 13 February 2021.[47] Gregory score two more goals for Derby before he suffered a season ending injury at the start of April.[48]
Sheffield Wednesday
On 5 August 2021, Gregory joined EFL League One side Sheffield Wednesday.[49] He made his Wednesday debut coming off the bench against Doncaster Rovers on 14 August 2021[50] and a few days later against Fleetwood Town he scored his first goal for the club.[51] Gregory won the EFL Player of the Month for April 2022.[52][53] Following promotion back to the EFL Championship an option was taken in Gregory's contact for him to stay at the club.[54]
Return to Mansfield Town
On 15 May 2024, Mansfield announced Gregory had returned on a one-year deal.[55] He made his debut on 9 August 2024, netting his sides second goal in a 2–1 victory over Barnsley.[56]
Career statistics
As of match played 29 December 2024
Appearances and goals by club, season and competition