Simon Heslop

Career Barnsley and loan spells Heslop began his career at Barnsley, where he progressed through the youth team and signed his first professional contract with the club in 2005. After playing regularly for Barnsley's reserve team, Heslop went on loan to Conference National club Kidderminster Harriers at the start of the 2005–06 season, on an initial one-month deal. The Kidderminster manager, Stuart Watkiss, was formerly Barnsley's academy manager, and stated – "He immediately caught my eye during my time at Barnsley, and he's a lad with a lot of natural ability". After impressing during his time with the club, the loan agreement was extended for a further month, and then once again in October. Heslop scored his first goal for the club on 5 November 2005, firing home a "sublime shot" in a 2–1 home defeat to Exeter City. The loan deal was extended until the end of January 2006, and Heslop returned to his parent club having made 27 appearances for Kidderminster during the season.

Having made no first-team appearances for Barnsley, After making four starting appearances during his month at Tamworth, before later being extended for the remainder of Tamworth's 2006–07 season.

In September 2007, Heslop spent a month on loan at Northwich Victoria, the third time he had been loaned out to a Conference Premier club. Just a week after returning from his loan spell at Northwich, Heslop joined divisional rivals Halifax Town on a one-month loan agreement. He made his debut as a substitute in a 1–0 defeat to Aldershot Town on 20 October 2007, and scored in the club's next match, a 3–1 win over Evesham United in the FA Cup. Just four days later, on 3 November, Heslop scored his second goal in as many matches, opening the scoring with a left-footed finish as Halifax comfortably beat Crawley Town at The Shay. Following a successful first month with Halifax, during which he scored twice in four matches, the loan deal was extended on 16 November, for a further two months until January 2008. A day later, Heslop scored a long-range effort as Halifax came from two goals down to beat Stevenage at Broadhall Way. After being a regular fixture in Halifax's midfield for the following two months, Heslop's loan was extended once more, this time until the remainder of 2007–08. He scored twice within the space of two weeks to take his goal tally to five for the season; before scoring the winner with a shot from 20-yards against Weymouth. He also scored the only goal of the match in a 1–0 win over Ebbsfleet United on 10 April, and made 40 appearances in all competitions for Halifax. However, no transfer materialised, and he had a trial with Port Vale later that month, although "budget restrictions" meant the deal collapsed. A week before the start of the new season, Heslop joined League Two club Grimsby Town on an initial three-month loan deal, with the option to join permanently after the period was over. On securing the loan signing, Grimsby manager Alan Buckley said – "He is a bit of everything, a box-to-box player. He's got a good chance of starting next week if he impresses in training". and went on to make 11 appearances during the three-month period.

In October 2009, over a year since his last first-team appearance for any club, Heslop was loaned out for a sixth time when he joined Kettering Town on a month-long deal. Heslop made five appearances during the month, as the loan was extended for a further month. He made 12 appearances during his time with Kettering, Two months later, Heslop signed for fellow Conference Premier club Luton Town on a 28-day emergency loan in March 2010. He was brought in to replace Luton captain Kevin Nicholls, who had been ruled out for the rest of the season. and scored his only goal for the club in a 4–0 win against Salisbury City at Kenilworth Road on 30 March. He made 13 appearances during his time with the club, including two appearances as Luton lost 2–0 on aggregate to York City in the Conference Premier play-off semi-final. Heslop was released by Barnsley at the end of 2009–10, having made just one appearance during his six-year association with the club.

Oxford United

Shortly after his release from Barnsley, Heslop joined League Two club Oxford United on a free transfer in June 2010. On signing Heslop, Oxford chairman Kelvin Thomas stated – "We are pleased to secure Simon's services. He is an excellent player and the encouraging thing about him signing is that he was made bigger financial offers at other clubs but wanted to come here". Just three days later, on 10 August 2010, Heslop scored twice in the club's 6–1 win over Bristol Rovers in the League Cup. He scored his first league goal the following month, netting with a 30-yard drive to open the scoring in an eventual 4–0 win over Morecambe at the Kassam Stadium. Heslop then scored with a "drilled right-foot shot" as Oxford secured a 2–1 home victory against Macclesfield Town on 28 December 2010. He added one further goal to his tally that season, scoring in the first-half from Jack Midson's cut-back in a 2–1 home win against Rotherham United in February 2011. Heslop scored five times, all at the Kassam, and made 40 appearances during his first season with the club. while the second came three days later when he scored a "stunning opener" from 35-yards out in a victory against Shrewsbury Town. Heslop scored yet another long-range strike in September that year, "thumping" Oxford ahead with an effort from 25-yards in a 2–0 win over Barnet at Underhill, his first goal away from Oxford's home ground. The goal ultimately turned out to be Heslop's last of the season, He remained at Oxford for 2012–13, and made 30 appearances as Oxford once again finished in a mid-table position. His only goal of the season came on 9 March 2013, scoring with a low shot in a 3–1 victory over Torquay United at Plainmoor. Shortly after the end of the season, in May 2013, Heslop was released by Oxford upon the expiry of his contract. During his three-year stay at Oxford, Heslop made 102 appearances and scored nine goals. He made his debut for the club on the opening day of 2013–14, playing the whole match as Stevenage lost 4–3 to Oldham Athletic at Broadhall Way. He scored his first league goal for the club away to Gillingham on 26 November 2013. On 12 May 2014, Heslop was released by Stevenage.

In August 2015, Heslop joined Torquay United.

He signed for Wrexham in January 2016.

York City

Heslop signed for his hometown club York City, who were newly relegated into the National League, on 20 June 2016 on a two-year contract. He captained York as they beat Macclesfield Town 3–2 at Wembley Stadium in the 2017 FA Trophy Final on 21 May.

Heslop requested a transfer in early November 2017, with manager Martin Gray dropping him from the team as a result. Heslop joined National League club Eastleigh on 16 November 2017 on a one-month loan. He made his debut two days later, starting in a 2–0 home defeat to Barrow. Heslop scored his first goal for Eastleigh in a 3–3 draw away to F.C. Halifax Town on 25 November 2017 with a shot from Chris Zebroski's cross. He made five appearances and scored one goal for Eastleigh, York manager Martin Gray reiterated that Heslop would not be considered for selection upon his return to the club.

Heslop was ruled out for the rest of the 2018–19 season in February 2019, with a knee injury that required a second operation. He was not offered a new contract at the end of the season but was invited to return for pre-season training.

Boston United Heslop signed for National League North club Boston United on 6 February 2020.

Blyth Spartans Heslop signed for National League North club Blyth Spartans on 26 August 2020.

Scarborough Athletic On 10 August 2021, Heslop signed for Scarborough Athletic. Following promotion to the National League North at the end of his first season, Heslop extended his contract till the end of the 2022–23 season. He departed the club in July 2023.

Later career In July 2024, Heslop joined fellow NPL Division One East side Bridlington Town. After one season with the club, he joined Northern Counties East Premier Division side Pickering Town.

Career statistics

Honours York City FA Trophy: 2016–17