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A striker signed on a three-year contract for an undisclosed fee from Southend United, just minutes before the transfer deadline in August 2007, making his debut in early September as a substitute in a televised defeat versus Yeovil, after a paperwork hitch prevented him from making his debut days previously. The defeat prompted manager Paul Sturrock to thrust Paynter into the starting line-up at Hartlepool the following week, and after a good team performance, Paynter marked his full home debut by notching a hat-trick against Bournemouth. Seemingly forging a formidable partnership with loan signing Simon Cox, Paynter scored a brace against Gillingham a fortnight later - Paynter admitted that he had surprised himself with the good start he had made.
When Paynter scored just once in his next nine appearances - ironically in the only match he didn't start, in the FA Cup at Wycombe - caretaker managers Dave Byrne and Ady Williams dropped him to the bench during December amidst talk of a crisis in confidence. Restored to the side in January after Barry Corr was suspended, Paynter was to net twice more in the cup in a third round replay at Barnet - firstly giving the Town the lead, and then inadvertently diverting the ball past Peter Brezovan early in the second half to equalise for the Bees - it only got worse when Paynter was one of four Town men to miss from the spot in the resulting penalty shoot out. The following week saw Paynter sidelined again, after being judged to have elbowed Crewe's Michael O'Connor - a claim Paynter denied, but his appeal failed, and a three game ban resulted.
Upon his return, Paynter netted his eighth goal for the Town against Cheltenham - his ninth wasn't to come until almost a month later, and again it was tainted by a sending off for deliberate handball, when he diverted a Huddersfield effort onto the bar. Though the Terriers scored the rebound, the referee had already blown and had little option but to send Paynter off - leaving nine man Town to hang on to a 3-2 lead for fifteen minutes, having been 3-0 up in the first half. This time, Paynter was benched on his return, and he started just two more games before the season's end - netting in a 2-1 win at Tranmere in March before starting the final game of the season.
With six strikers vying for the two attacking roles at the start of the 2008/09 season, Paynter was given the nod to start up front with Simon Cox again - and as the season progressed, the understanding between the two improved further - Paynter's strong play matching the pace and intelligent running of Cox well. Thougx was obviously the main goalscorer, Paynter himself started the season well, with three goals in his first five games. Though he was regularly substituted to make way for other attacking options, it was December before Paynter found himself out of the first eleven, and this was a self-inflicted wound, as he was sent off at Crewe for the second season in succession. The resulting suspension could not have come at a worse time for Paynter, as new manager Danny Wilson was appointed over the Christmas period that Paynter missed.
Injury to Barry Corr though was to hand Paynter his place back in January, and from that point, he was ever-present in the side for the rest of the season, as the Town clawed themselves out of relegation trouble. Paynter finished the season with twelve goals in all competitions, but his Golden Boot winning striker partner Cox was the first to praise Paynter for his unselfish contribution to his total, saying that he wouldn't have been anywhere near the top of the goalscoring charts without Paynter alongside him.
After Cox left For West Brom over the summer, Paynter started the 2009/10 season as a lone striker, and he went on to partner loan signings Tope Obadeyi, Ben Hutchinson and Alex Revell as Wilson searched for a prolific partnership to match the previous season. Paynter failed to live up to his form in that campaign, and after notching just two league goals in the opening two months of the season, he was dropped to the bench in October. During the period he was out of the starting eleven, the Town won just one and lost two of the four games - and when Paynter scored twice in a 4-1 reserve win at Reading (partnering a new signing from non-league, Charlie Austin), he was recalled for a match at Tranmere, and scored twice more in another 4-1 victory. It was the last time that Paynter would be dropped from the side. Three weeks later, Austin was called up to the starting eleven for the first time, and the two players struck up an immediate understanding - and though Austin was grabbing the headlines with his rags-to-riches story, it was Paynter who was scoring the most goals - netting fifteen goals in a seventeen match run from the end of November through to April. During this time, Bristol Rovers were linked with a move for him during the January transfer window, shortly before Paynter was named as the League One Player of the Month for January - an award he was also nominated for again in March - and Paynter also entered negotiations over a new contract. However, after Paynter netted twice at Elland Road in a superb 3-0 win against Leeds (taking his tally up to four against the Whites in the two games), the rumour mill was already in full swing, suggesting that Leeds were getting ready to swoop for the striker at the end of the season - and when Paynter failed to appear for the first leg of the play-off semi-final in May, conspiracy theorists were suggesting that a deal had already been done, and Paynter wasnít playing to avoid injury.
This was proven to be false when Paynter returned for the second leg, but obviously not 100% fit from a hamstring injury, he didnít really do himself justice - being substituted in both the match at Charlton and the final at Wembley, as the Town narrowly missed out on promotion - Paynter finishing his best season in a Town shirt on 29 goals; his partnership with Austin yielding 42 goals in the last six months of the season. Days later, Paynter turned down an improved contract offer, and chairman Andrew Fitton admitted that his departure was inevitable - the following day it was announced that Paynter had agreed to join Leeds when his contract expired.
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