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On 25 June 2019, Gregory joined Championship side Stoke City.

Gregory signed a contract extension with Millwall in September 2016. Millwall were involved in a tense fight for a play-off place through out the season, eventually securing their place with a 4–3 final day success over Bristol Rovers, with Gregory scoring twice. 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. 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. 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. At the end of campaign, his contract was extended by Millwall for an extra year after the club exercised an option. He played 50 times in the 2018–19 season, scoring 13 goals helping the side successfully avoid relegation, finishing in 21st position. Gregory left the Den at the end of the season with him expressing his desire to move back up north.

On 16 June 2014, Gregory signed a three-year contract with Championship Millwall after the club agreed a fee with Halifax. He scored his first Football League goal on 30 September 2014 in a 3–1 home defeat against Birmingham City. 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. 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. Gregory scored on the opening day of the 2015–16 season, in a 2–1 victory over Shrewsbury Town. He scored four goals against Plymouth Argyle in the EFL Trophy on 10 November 2015. 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.

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. 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. On 30 June 2013 Gregory signed a new two-year deal with Halifax, 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. During the January transfer window Gregory nearly moved to Crawley Town. At the end of the campaign Gregory was attracting interest from Football League clubs with Championship side Millwall making a number of bids.

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. 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. 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.

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. 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.

Gregory started playing football at the Sheffield United Academy. He was not offered a professional contract with the Blades and so he went and played non-league football with Staveley Miners Welfare whilst learning to become an electrician. After a prolific season with Staveley he joined Mansfield Town in September 2009. He failed to break into the first team at Field Mill and after loan spells with Glapwell, Harrogate Town and FC Halifax Town he signed for the later on a permanent basis. He became a regular goalscorer at The Shay helping them win the Northern Premier League Premier Division title in 2010–11 and promotion from the National League North via the play-offs in 2012–13. His goals earned him a move to Championship club Millwall in June 2014. Gregory scored 27 goals in 2015–16 and helped the Lions beat Bradford City in the 2017 EFL League One play-off Final. He scored 77 goals in 238 appearances for Millwall before joining Stoke City in June 2019.

Born in Sheffield, Gregory played for the Sheffield United Academy and was released in 2008. Following his release from the Blades' academy Gregory, began working as an electrician whilst playing for Northern Counties East League side Staveley Miners Welfare. He scored 37 goals in the 2008–09 season with Staveley which saw him attract interest from higher placed clubs.

Lee Andrew Gregory (born 26 August 1988) is an English professional footballer who plays as a striker for Championship club Stoke City.