Port Vale

Paynter started his career at Port Vale after being scouted in his native Liverpool at the age of ten.^[3] He signed professional forms in 2000, and manager Brian Horton gave Paynter his debut against Walsall at Vale Park on 3 May 2001. At only 16 years and 294 days old, this made him the youngest Vale player for twenty years.

Horton went on to give the young striker seven further Second Division games in the 2001–02 season. He scored his first senior goal past Notts County on 17 September 2002, making him the club's youngest goalscorer for 24 years. By the end of the season he had scored five goals in 34 appearances. Still a teenager during the 2003–04 season, he hit 14 goals in 48 games despite being played mostly on the right-wing, leaving him second in the club's scoring charts behind the prolific Stephen McPhee.^[3] He was rewarded with a long-term contract at the season's end.^[4]

He opened the 2004–05 season by being sent off for over celebrating after scoring Vale's first goal in a 3–2 defeat at Walsall on 7 August; he went on to criticize referee Lee Probert for ruining the game with the red card decision.^[5] He went on to end the campaign as the club's top-scorer with thirteen goals in fifty games; this came despite criticism from some supporters for a mini-goal drought in mid-season.^[6] In March, manager Martin Foyle dismissed rumours of Paynter moving to nearby Crewe Alexandra.^[7] At the end of the season, fans voted Paynter as the club's Player of the Year.^[8] He started the 2005–06 season with just two goals in sixteen League One games, but had still done enough in his Port Vale career to justify a move into Championship football. The club reported Tony Pulis' Plymouth Argyle to The Football Association for an alleged illegal approach for the player,^[9] but accepted a bid from Hull City.

Hull City

In November 2005, Hull City manager Peter Taylor signed Paynter on loan,^[10] then later negotiated a permanent transfer for an initial fee of £150,000 in the January transfer window.^[11] Teammate Sam Collins also moved to Hull at the same time. Again, Paynter mainly played as a striker, but also made some appearances as a right midfielder. He scored three times in his 23 appearances, before moving on again at the end of the season.

Southend

Paynter joined Southend United on a three-year contract on 7 August 2006 for an undisclosed fee,^[12] although he actually joined the Shrimpers a few days earlier on loan, to enable him to play in their match against Stoke City.^[13] Paynter scored his first and what turned out to be only Southend goal in a 3–2 League Cup victory over Brighton,^[14] but lost his place in the first-team due to a lack of goals.^[15] Paynter's stay at Southend was brief, interrupted by a hamstring injury, and on the last day of the January transfer window of the 2006–07 season he was loaned out to Bradford City for a month,^[16] having made just eleven appearances for Southend.^[17]

Paynter made his debut for Bradford City against Nottingham Forest on 3 February 2007, scoring a last minute equaliser to earn the Bantams a 2–2 draw.^[18] He played fifteen times for Bradford, scoring four goals, after his loan was extended to the end of the season.^[19]

Swindon Town

In August 2007, Paynter signed for Swindon Town on transfer deadline day on a three-year contract.^[20] He made his debut on 9 September, coming on as a substitute in a televised defeat against Yeovil.^[21] He hit a hat-trick against AFC Bournemouth on 22 September,^[22] his first game at the County Ground.^[23] He followed this up with a brace against Gillingham in a 5–0 win on 6 October, as a strong partnership with loan signing Simon Cox began to develop.^[24] Following Paul Sturrock's departure, caretaker managers David Byrne and Maurice Malpas dropped him over concerns that he had lost confidence following a run of one goal scored in nine games.^[23] He was soon returned to the starting line-up after Bradley Orr picked up a suspension.^[23] In January, he scored a goal and an own goal in an FA Cup replay with Barnet,^[25] before he was sent off in a League One game with Crewe Alexandara for an elbow on Michael O'Connor.^[26][23] He was sent off again in March for a deliberate handball against Huddersfield Town, and ended the 2007–08 season with ten goals in forty games.^[23]

Paynter made 42 league starts in the following 2008–09 season for Swindon, scoring eleven goals and providing vital support for the league's joint top-scorer Simon Cox.^[27] His strong play was a good foil for the pace and intelligent running shown by Cox.^[23] However, another sending off against Crewe Alexandra tarnished his reputation for new manager Danny Wilson.^[23] He did though regain his first-team spot after Barry Corr picked up an injury in January.^[23]

Cox was sold to West Bromwich Albion in summer 2009, and Paynter was given a more prominent role in attack as a result of his departure. He netted fifteen goals in a seventeen match run from the end of November through to April. Paynter was named as the League One Player of the Month for January^[28] – an award he was also nominated for again in March – and at this point Paynter also entered negotiations over a new contract with Swindon. On 3 April 2010, Paynter scored a brace for Swindon in their 3–0 rout of Leeds United at Elland Road – the win gave Swindon some hope of achieving automatic promotion. He had also previously scored twice against Leeds that season in a 3–0 win at the County Ground.^[27] Swindon reached the League One play-offs, and won their play-off semi final after beating Charlton Athletic on penalties – Paynter had missed the first leg through injury, but returned for the second leg which saw Swindon edge into the final at Wembley. He overcame a slight injury doubt and managed to play from the start in Swindon's 1–0 defeat to Millwall, with Paynter being substituted late on in the second half.^[27] During the 2009–10 season, Paynter also managed to form a formidable strike partnership with fellow striker Charlie Austin, as the pair scored a total of 49 goals between them.^[29] In total Paynter scored 29 goals for Swindon during the 2009–10 season, representing his best goal scoring ratio in a single season.^[27]

Leeds United

In June 2010, after turning down a new deal at Swindon Town,^[30] Paynter accepted a three-year deal with newly promoted Leeds United.^[31] In late July however, it was reported that Paynter would be ruled out for two-months after suffering a stress fracture of the shin that he had picked up during Leeds' pre season schedule. The injury ruled him out of the rest of the pre-season, with manager Simon Grayson suggesting that the club could not provide and timescales on Paynter's recovery from injury. Paynter finally returned to training at the start of September, and played 90 minutes in a behind closed doors friendly,^[32][33] however, Paynter later suffered a reaction to his injury, keeping him out of action longer than had been expected.^[34]

Having finally returned to fitness and having appeared for Leeds' reserve team,^[35] Paynter finally made his first-team debut on 10 October 2010, as a second-half substitute in a 4–1 defeat of Scunthorpe United.^[36] Paynter eventually scored his first goal for Leeds in a 2–1 win at Preston North End on 8 March.^[37] Paynter had a disappointing first season with Leeds, scoring just once in 23 games, and was linked with a move to Yorkshire rivals Sheffield United during the following the summer.^[38]

Having remained at Leeds despite interest from elsewhere, Paynter came on as a substitute for Leeds on the opening day of the 2011–12 season as they suffered a 3–1 defeat against Southampton.^[39] Paynter was unable to establish himself in the Leeds first-team however, as he picked up another injury, sidelining him for a further spell.^[40] At the end of August, Paynter was given permission to speak with Brighton & Hove Albion regarding a move to the club.^[41] However, decided to stay at Leeds and fight for his place in the team.^[41] With Luciano Becchio returning from injury and the signing of Mikael Forssell, Paynter's playing opportunities diminished further, and manager Simon Grayson hinted that he would allow Paynter to go out on loan.^[42]

Having not played since the opening day of the season for Leeds, in October 2011 reports circulated that several Championship clubs were interested in taking Paynter on loan.^[43] but Leeds insisted they would not loan him to a rival club in the same division, and were currently considering an offer from an unnamed League One side.^[44] On 27 October 2011, Paynter signed for Brighton & Hove Albion on loan until the start of January 2012.^[45] He made his debut for the club on 29 October, as a second-half substitute against Birmingham City.^[46] He played a total of ten games for Brighton without scoring before he returned to Elland Road.

Paynter finally made his first start of the season for Leeds, and his first start under new manager Neil Warnock in mid April 2012, coming into the side against Peterborough United, scoring twice in a 4–1 home win.^[47] He was given a second consecutive start in the following game against Blackpool, however, he picked up an Achilles injury in the game which ended his season prematurely.^[48] Neil Warnock subsequently placed Paynter on the transfer list at the end of the 2011–12 season.^[49]

Doncaster Rovers boss Dean Saunders was strongly linked with a move for the striker at the end of July.^[50] However, Paynter instead joined Blackpool for a week-long trial.^[51] The trial was cut short after a few days, and he began training with Doncaster Rovers.^[52] When Leeds issued their squad numbers for the 2012–13 season on 3 August, it was revealed that Paynter, previously the club's number nine, had not been allocated a number.^[53]

Doncaster Rovers

Following a trial spell, Paynter completed a free transfer to League One side Doncaster Rovers on 13 August 2012, signing a two-year contract.^[54] Paynter scored 13 goals in 40 games during the 2012–13 campaign, and on the last day of the season he provided the pass to James Coppinger which was converted for the late winning goal over Brentford that won Doncaster promotion to the Championship as champions of League One.^[55]

On 10 January 2014, Paynter signed for Sheffield United on loan.^[56] He spent most of his time on the bench as Nigel Clough chose to use Jose Baxter as a false number nine in a highly successful run that took the club up the table and into the semi-finals of the FA Cup.^[57] played 13 games for the "Blades" in the second half of the 2013–14 campaign, without scoring a goal. He was released by Doncaster manager Paul Dickov in May 2014.^[58]

Carlisle United

Paynter signed a two-year contract with newly-relegated League Two club Carlisle United in June 2014.^[59] It was reported that he decided to reject higher paid offers from clubs in higher divisions in join the "Cumbrians" after being convinced to come to Brunton Park by manager Graham Kavanagh.^[60] However, Carlisle struggled during the 2014–15 season, and after being fined by new manager Keith Curle for refusing to take part in extra training sessions put on for players not in the first-team, both Paynter and Gary Dicker took representation from the Professional Footballers' Association to dispute the legality of their fines.^[61] He was transfer listed by Curle in May 2015.^[62]

Hartlepool United

Paynter had his contract with Carlisle United cancelled by mutual consent and joined League Two rivals Hartlepool United on 27 June 2015.^[63] He was appointed as club captain by manager Ronnie Moore.^[64] He made his debut in the 2–0 win over Morecambe in the first game of the 2015–16 season, scoring the opening goal and providing an assist for Rakish Bingham.^[65] Three days later, Paynter scored in his second game to help Hartlepool beat Fleetwood Town 1–0 in the first round of the League Cup.^[66] His total of 15 goals in 35 appearances in the 2015–16 season made him the club's top-scorer and caused new manager Craig Hignett to exercise a contract clause to keep Paynter at the club for another year.^[67][68] He was out injured in January with an Achilles problem, and underwent surgery to correct the issue two months later.^[69] Hartlepool were relegated into non-League at the end of the 2016–17 season, and Paynter admitted that he did not know what manager Dave Jones had been doing with his tactics.^[70] Paynter was one of three men – along with Stuart Parnaby and Ian Gallagher – tasked with assisting caretaker manager Matthew Bates for the final two games of the season, which ended in a defeat and a victory, but ultimately relegation.^[71] Paynter was released in May 2017.^[72]

Warrington Town

On 26 November 2017, Paynter signed with Northern Premier League Premier Division club Warrington Town.^[73] He had previously been training with AFC Fylde and Southport.^[74] However, he announced his retirement from football the following month.^[75][76]