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Gregory returned to England and rejoined Lewes on 7 September 2019.

In 2018, Gregory returned to America to sign for National Premier Soccer League side Orange County and he continued to play for the club in the 2019 season too.

In March 2014 Gregory had a trial at Charlton, but nothing came of it.

In May 2014 Gregory joined USL Premier Development League side Ventura County Fusion. He made his debut for the club on 8 May, and scored the winning goal in their first round US Open Cup game, a 2–1 win over CD Aguiluchos.

On 12 July 2014 Gregory switched teams and countries again, signing a one-year deal with S.C. Beira-Mar. He made his debut for the club on 17 August, replacing Bilal Sebaihi in the 78th minute of a 0–1 away loss against Oriental for the Segunda Liga championship. On 11 December 2014, Gregory announced on his official site that he had left the club.

Gregory made his first team debut on 7 August, replacing John Utaka in the 83rd minute of a 0–2 Championship away loss against Coventry City. He appeared in further twelve minutes in a 2–1 away success against Stevenage for the Football League Cup two days later, and featured on the bench in a 1–1 home draw against Reading on 14 August.

On 15 November, Gregory signed a contract with Eastbourne Borough. However, after being sparingly used, he joined Lewes in March 2012.

Gregory made no further appearances for Pompey during the campaign, and was released along with nine players on 15 May 2011.

Gregory signed a one-year professional deal with Portsmouth on 1 July 2010, being assigned number 39. He played in pre-season matches against Fulham and Bournemouth, and was also taken on the club's North American Tour playing against Club America, D.C. United, FC Edmonton and Ventura County Fusion.

Born in Eastbourne, Gregory started his footballing career at Brighton's youth setup before moving to Portsmouth Academy; after being offered a scholarship deal with the latter in June 2008, he was a regular first choice in the Premiership Reserve League. He won man of the match awards in FA Youth Cup twice, whilst being also first-choice left back with the under-16s and first-choice right back with the under-18s.

Peter Gregory (born 25 July 1992) is an English footballer who plays for Lewes. He is a full back capable of playing on either flank, he can also play as a winger.