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With his first team opportunities limited at Morecambe, Sampson joined Macclesfield Town on loan until the end of the season. Two days after signing for Macclesfield Town, Sampson the made his Macclesfield Town debut, coming on as a substitute for Waide Fairhurst in the 84th minutes, in a 0–0 draw against Bristol Rovers. Sampson scored his first goals in the next game, in a 2–2 draw against Halifax Town on 3 April 2015. After making four appearance and scoring times, Sampson returned to his parent club and was released by the club at the end of the 2014–15 season.

In June 2015, Sampson rejoined Macclesfield Town on a permanent deal.

On 25 July 2013, Sampson joined Morecambe on a two-year contract after being released by Bolton Wanderers.

Sampson made his Morecambe debut in the opening game of the season, in a 1–0 loss against Wycombe Wanderers. Sampson then played a role when he provided two assists, in a 2–0 win over Exeter City on 24 August 2013 and scored his first goal for the club on 7 September 2013, in a 3–1 win over Southend United. After the match, Manager Jim Bentley was impressed with Sampson's display at the start of the season and believed he deserved to score his first goal. His second goal later came on 5 October 2013, in a 4–3 win over Chesterfield. His fourth and fifth goal later came against Accrington Stanley on 26 October 2013 and Hartlepool United respectively. In his first season, Sampson was a first team regular and scored five times in forty-two appearance.

In his second season at Morecambe, Sampson made a good start when he provided an assist for one of the goals in the game, in a 4–0 win over Dagenham & Redbridge in the opening game of the season. However, Sampson struggled for first team opportunity behind Jack Redshaw, Kevin Ellison, Paul Mullin and Pádraig Amond before suffered a foot injury that had kept him sidelined for a month.

Sampson joined Southend United on loan for one month on 12 January 2012 after signing a new 18-month contract at Bolton. He was given the number 26 jersey for the duration of his loan period, and made his debut on 14 January when coming on as a late substitute for Elliot Benyon in Southend's 5–2 victory at Northampton Town, where he gained an assist. On 13 February the loan was extended for a further month. This loan was extended for another month on 12 March. Sampson was given the number 37 shirt for the Championship season.

On 11 October 2012, Sampson joined Accrington Stanley on a one-month loan deal to gain some more experience and to link up with former Bolton full back Leam Richardson who had been installed as manager that week. Despite Accringtons best efforts to keep him he returned to his parent club at the end of his loan spell in November 2012 after making 6 appearances to try and catch the eye of new manager Dougie Freedman who had been appointed during his absence.

Sampson was released by Bolton, along with several other youth players at the end of the 2012–13 season.

In September 2011, Sampson received a call-up by the England U19 squad.

Sampson came through the Wigan Athletic academy, before joining Bolton in 2008 and a number of other youth players. Around this time, Sampson was soon attracted a move away from Bolton Wanderers at age fifteen at the time after linked with a move to big clubs.

Jack Sampson (born 14 April 1993) is an English professional footballer who plays as a forward for Southport. Sampson played for Bolton Wanderers and for Morecambe. He has been capped at England Under-19 level. He attended Cansfield High School in Ashton-in-Makerfield.