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A left sided winger originally signed on a loan deal until the end of the season in February 2010, after an attempt to sign him permanently during the January transfer window was thwarted by the perilous state of Portsmouth's finances - Ritchie went on to make just four substitute appearances at Swindon during his first spell at the club, his debut coming in a 4-1 win over Stockport on 23rd February, when he replaced the injured Danny Ward just twenty-five minutes into the game.
Just over a month later, after scoring a hat-trick for the reserves against Exeter, Portsmouth recalled Ritchie from his loan spell, having gone into administration, to put him straight into their squad for their Premier League game at Tottenham.
Over the summer, with Wilson once again showing interest, Ritchie stated that he wanted to stay at Portsmouth - with Pompey relegated to the Championship, he wanted the chance to prove himself for his home town club. In October though, manager Danny Wilson returned to Pompey for Ritchie again, signing the winger on an initial month's loan - and this time he was thrust straight into the team for a 2-0 Johnstone's Paint Trophy win over Torquay. After notching his first Town goal in a 5-4 defeat at Peterborough eleven days later, Wilson was quick to extend Ritchie's loan for another month - and as he continued to impress in a side not living up to expectations, his deal was again extended to the maximum three month period for a short-term loan. With Pompey in severe financial difficulties though, there was some worry that they may recall him - especially with two of their own players within one game of triggering a loyalty payment. However, when Portsmouth confirmed that they would not be renewing Ritchie's contract after all, and after the winger scored goals in back-to-back games in the New Year, Swindon finalised a deal to bring the winger to the County Ground on a permanent basis, signing a two-and-a-half year deal for an undisclosed fee believed to be in the region of £200,000.
Ritchie went on to be virtually ever-present for the rest of the campaign - the only game he didn't start, a 1-1 draw against Rochdale in February, he was introduced as a first-half substitute for the injured Alan O'Brien. Ritchie's performances were one of the only bright spots in an otherwise awful season - after the departure of Charlie Austin in January, Ritchie became the club's top scorer for the season (despite only scoring eight times in all competitions) - and with the Town relegated, Ritchie picked up both the Swindon Advertiser and Supporters' Club Player of the Year awards. Despite rumours of Championship clubs chasing him over the close season, Ritchie was one of a handful of players who remained at Swindon for the club's League Two campaign.
With new Town boss Paolo di Canio employing Ritchie in a different role for the start of the new season, by his own admission, Ritchie didn’t have the best of starts to the new campaign – preferring his wide players to cut inside, di Canio switched Ritchie over to the right flank, where his partnership with Paul Caddis became arguably the most important part of a successful Swindon side. After receiving bookings in the opening three games, Ritchie netted in the next two league matches – the first an equaliser in the local derby against Oxford, the next an opening goal at Shrewsbury – both games that Swindon went on to lose, leaving them in a lowly 21st position in the table.
By the end of September, Swindon’s form had picked up, with Ritchie’s partnership with Caddis a major influence – prompting di Canio to describe him as “one of the best players in League Two”, and chairman Jeremy Wray to state that Swindon would do everything they could to keep the winger at the County Ground when the transfer window opened in January. Though Ritchie sometimes opted for the selfish or spectacular option when other, perhaps better, opportunities were present, regularly this approach paid off for him. He netted twice more in a 4-0 win over Barnet – the second a superb solo effort – the following week though, he was at the centre of controversy at Macclesfield – with the Town a goal down, Ritchie looked set to score at the Moss Rose ground, but as he rounded José Veiga, the Silkmen’s keeper nudged him. Though Ritchie attempted to keep his feet to tap into the empty net, he wasn’t able to – when the referee failed to award the spot kick, it led to di Canio publicly telling his players that in future, they should dive in the same situation. At the end of October, a superb thirty-yard strike from Ritchie broke the deadlock against Gillingham – a goal that di Canio described as eclipsing many of those that he had scored himself in the Premier League. Soon afterwards, Ritchie stated that he was enjoying every minute of his time under the Italian, and that he was ignoring any transfer speculation.
At the end of November though, the speculation came to fruition, as Swindon received the first bid for his services – a loan offer from Bournemouth with a view to a permanent £250,000 transfer. Ritchie stated that “his mind was on the job” – and followed that up with a superb strike at Colchester that sealed a victory over their League One opponents in the FA Cup. Victory over Southend in the Johnstone’s Paint Trophy Area Semi-Final came at a price for Ritchie – a booking picked up during the game resulting in suspension – Ritchie missing his first game of the season at Bristol Rovers. Over the Christmas period, Bournemouth renewed their interest in anticipation of the transfer window – tabling a £500,000 deal for the Town winger – when this too was rejected, Cherries director Tom Mitchell announced that their interest was now over.
However, after January saw Ritchie assist two goals as the Town beat Premiership Wigan in the FA Cup and then net two more superb strikes in a 2-1 victory at Rotherham (goals that saw him named in the League Two team of the week), Championship club Ipswich were rumoured to be preparing a double bid for both Ritchie and Caddis – rumours that were soon scotched by Town chairman Jeremy Wray – but on transfer deadline day itself, Bournemouth again returned with a renewed offer. The rumour mill went into overdrive – and with Swindon in a promotion clash at Southend that evening, it was initially thought that Ritchie had not travelled with the squad, rumours that were soon proven false, as Swindon again rebuffed the Cherries’ approach. With the speculation finally off his back, Ritchie gave a superb performance at Roots Hall – scoring once and assisting two other goals as Swindon recorded a superb 4-1 victory that moved them into the promotion places for the first time since the opening day.
Swindon won all of their matches throughout February, as they cemented their place at the top of the table, and also won a place at Wembley in the Johnstone’s Paint Trophy, beating Barnet in the Area Final. When the ten match winning League run came to an end at Oxford in March, Ritchie was unlucky with a shot from distance that hit the post, and was also involved in an altercation with a ballboy, as the Town’s local rivals tried every trick in the book to register their victory.
Two weeks later, Ritchie’s superb form was recognised by his peers, as he was named as the League Two Player of the Year – ironically though, the award came at a time when Ritchie’s form was at the lowest level it had been since the start of the season – after Paul Caddis hobbled out of a 4-0 victory over Dagenham, Ritchie found himself without his usual attacking support on the right flank, and was often double-marked as a result. Nowhere was this more obvious than at Wembley, as League One Chesterfield contained a frustrated Ritchie throughout the Johnstone’s Paint Trophy Final – the Spierites running out as 2-0 victors.
The following weekend, Ritchie looked back to his best against Bristol Rovers, only to be withdrawn in the second half with an ankle injury which kept him out for three weeks – in his absence, Swindon got themselves to the very brink of promotion. Needing just one point to secure League One status at the first time of asking, Ritchie returned for the trip to Gillingham where he was paired up with Caddis for the first time in over six weeks – despite this, Swindon slumped to a 3-1 defeat, but secured promotion due to results elsewhere. The following weekend though, the partnership clicked once again – Ritchie scoring a superb opening goal as the Town thumped Port Vale 5-0, to secure the League Two championship – just days after both Caddis and Ritchie were named in the League Two Team of the Year. With the title secured, Ritchie paid tribute to di Canio’s feat of turning the club around, and stated that he expected Swindon to be challenging for honours in League One the following season.
Over the summer, Bournemouth returned again with a renewed bid for Ritchie - this time, the Town turned down a £900,000 offer - and his superb form continued into the new season, as the winger netted five times in the first five weeks of the season, despite missing one game through injury - including strikes against former club Portsmouth, and two against his potential suitors in a 4-0 win over the Cherries at the County Ground. It was during this time that Ritchie agreed a year’s extension to his contract at the club - taking him to the summer of 2014.
During October though, by his own admission, Ritchie’s form took a turn for the worse - and after being substituted in a game against Coventry with the Town 2-0 down (a game they went on to draw), he was unusually left out of the starting eleven for a defeat at Crewe. The following weekend, Ritchie was restored and seemed back to his best, as he netted again in a 4-0 win at Stevenage - and he scored three more before the year was out, as the Town challenged at the top of the table.
When the transfer window opened in January, rumours again surfaced about Ritchie leaving the club - and when reports linked Championship side Crystal Palace to the winger, boss di Canio again reiterated that he wasn’t for sale - joking that while he thought £20 million might be crazy money, he might accept £15m. Incredibly though, after appearing in a goalless draw at Leyton Orient at the end of the month, the following day it was announced that a move to Bournemouth had been agreed, for a cut price fee of £500,000 - with the club in the middle of a takeover deal, and unwilling to put any more money in, owner Andrew Black agreed with the incoming consortium to sell the winger to fund the club during the handover period - and with the Cherries the only club willing to stump up the cash immediately, a shocked Ritchie agreed the transfer to Dean Court. It was later revealed that di Canio only discovered the deal was going through when Ritchie called him - the Town boss believing it was a joke at first - and though the Italian first seemed to accept it, he later stated that the transfer was in breach of his contract - three weeks later, he resigned. Come the end of the season, it was Bournemouth that were promoted to the Championship and not Swindon, Ritchie winning the League One Player of the Year award to add to his League Two award from the previous season.
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