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He scored on his debut for Dundee, a 4–0 win against Peterhead in the first round of the Scottish League Cup. Ferry made his league debut for Dundee, in the opening game of the season, in a 1–1 draw against Kilmarnock. However, his time at Dundee were shattered over suffering injuries twice. Despite the injuries, Ferry made twenty-two appearances and scored once in all competitions. On 31 August 2015, he was released by from his contract by mutual consent.

Ferry signed for Scottish League One side Peterhead in September 2015.

In June 2014, he joined Dundee and spent just over one year at the club before joining Peterhead.

On 7 June 2014, Ferry moved back to Scotland, where he signed for Dundee, becoming the sixth signing of the season, ahead of their Scottish Premiership campaign, following their promotion. Upon the move to Dundee, Manager Paul Hartley said that signing Ferry would boost the club's attack saying: "He played the last year as a sitting midfielder but I see his strengths in attacking and going forward with the ball. He is young and dynamic and has proved himself in England at a very decent level."

On 25 July 2013, Ferry signed a two-year contract with Portsmouth, on a free transfer. Upon joining Portsmouth, Manager Guy Whittingham described Ferry as someone he needs, due to being "extremely fit and his work-rate is fantastic, something our fans demand" He's also somebody who can link play, be defending our box one minute and the next attacking the opposition. I think his all-round game is very good. Simon is a big part of what we want to achieve."

He made his debut in a 4–1 home defeat to Oxford United on 3 August 2013. On 14 September, Ferry scored his first Pompey goal, in a 2–1 away victory over Burton Albion. After scoring against Burton Albion, Ferry believes the club need to perform well if they were to become a serious contender in League Two. Ferry was, at the time, started every league game for the Blues until he sustained a hamstring injury.

After missing out three games, Ferry made his return on 26 October 2013, as Portsmouth drew 1–1 with Torquay United. After the draw with Torquay United, Ferry was happy to make his return after being on the sidelined. The next game against Exeter City, on 2 November 2013, Ferry was captain when they won 3–2. Ferry would sustained a hamstring and back injury that kept him out for months. After three months out, Ferry made his return and was captain, as Portsmouth won 1–0 against Hartlepool United. Ferry was captain again during a match against Dagenham & Redbridge in the next game. But during the match, Ferry forced to come off in the 38th minute and was substituted, though Portsmouth would win 4–1. After the match, it announced that Ferry missed the rest of the season because of his back injury.

The next season, with the club's promotion return to League One, Ferry continued to maintain his first team place at Swindon Town. For the first time, Ferry was named in League One Team of the Week on 1 October 2012 when he scored his first goal for the club, which was the only, as Swindon Town would win 1–0 against Shrewsbury Town. Following his first goal for the club, Ferry stated he is expected to score at least four-five goals this season on a more regular basis. In November, Ferry was handed in as captain, ahead of a match against Macclesfield Town in the first round of a FA Cup, but lost 2–0. Shortly this, Ferry scored his second goal of the season, in a 2–0 win over Walsall and the following week, he also provided quadruple assist for Andy Williams and Darren Ward, in a 4–1 win over Yeovil Town. In the last two games in early March, Ferry started playing in right side of midfield, under newly manager Kevin MacDonald, mainly due to lack of midfields, who plays in right midfield. This was extensively denied by MacDonald. Ferry then scored two goals in two consecutive games, against Walsall and Brentford. In a match against Brentford, Ferry was, once again, named in League One Team of the Week for the second time on 12 March 2013.

Having featured for eight out of nine games for Swindon Town, Ferry overly praised Di Canio's squad selection and was then immediately dropped from his first team plan. Di Canio praised Ferry on his home form, describing him as the main player that pressed everywhere and challenged every ball. Ferry scored his first goal, in his return and first since moving to Swindon permanently, in a 3–3 draw against Hereford United on 8 October 2011. A month later, Ferry scored his first FA Cup goal, during a 4–1 defeat of Huddersfield Town of League One. In a 2–1 win over Wigan in the third round of the FA Cup, Ferry was among awarded Ronnie Radford Award, with the squad

Ferry scored a hilarious own goal in Swindon's play-off semi-final win over Charlton Athletic in May 2010. However, Swindon would only lose to Millwall in play-off final, missing out to be promotion to the Championship and Ferry making a start for the final. Despite the loss, Ferry stated playing in Wembley is his stage in my career, describing as "need to jump one way or the other" At the end of the season, Ferry was recalled by parent club, Celtic, according to the club's chairman Andrew Fitton

On 2 August 2010, Ferry signed a permanent deal with Swindon, along with Celtic teammate, defender Paul Caddis. Ferry previously stated his wanted his move to Swindon Town turned to a permanent deal. Shortly after the permanent move, Ferry says his moving to Swindon permanently is a relief after the move was described as "deed in the water".

Ferry's first game after signing for the club on a permanent basis came in the opening game of the season, coming on as a substitute for David Prutton, in a 2–1 loss against Brighton & Hove Albion. A month later, Ferry went on the sidelines, having suffered a mysterious ankle injury in training, which left him out for two weeks. He returned from "injury" on 28 September 2010, coming on as a substitute for Thomas Dossevi, in a 3–2 loss against Plymouth Argyle. Since then, Ferry has featured on the bench, being un-used, as he made 21 appearances. The club was then relegated after losing 3–1 against Sheffield Wednesday. This incident led to Ferry and Hart falling out and revealed that Ferry considered quitting the club.

Ferry started his career with Scottish Premier League club Celtic but never played a competitive match for the first team. He spent the 2009–10 season on loan at Swindon who then signed him permanently at the end of the deal for £300,000. He then moved to Portsmouth.

His professional development was curtailed by injury problems sustained in the 2006–07 season, which resulted in his missing almost three years of club football. He returned to the Celtic first team squad in February 2009, and featured in a 2–0 win in a Wembley Cup match against Tottenham Hotspur on 26 July 2009. Ferry later told BBC Wiltshire that his professional development would end his career because of his ongoing ankle injury.

On 27 August 2009, Ferry joined Swindon Town on loan until January 2010 along with Celtic teammate Ben Hutchinson. He made his debut for Swindon on 29 August, receiving the Clubs Man of the Match award in a 2–1 victory against Southend United. Two months later, after his debut, he scored his first goal for the club, on 31 October 2009, in a 4–1 win over Tranmere Rovers.

A week after scoring his first goal, on 26 November 2009, it was announced that a deal had been agreed with parent club Celtic to extend the loan until the end of the season. Ferry stated he would like to stay at the club and revealed he has adapted easily to life on and off the pitch at Swindon Town. Soon on 23 February 2010, Ferry scored his second goal for the club, in a 4–1 win over Stockport County. After the match, Ferry says he blacked out when he scored and doesn't remember how he scored during the match.

Due to injury, he missed the 2007 FIFA Under-20 World Cup.

Ferry has played for the Scotland national under-19 football team and featured for them at the 2006 European Under-19 Championship.

Having played for the Celtic youth teams, Ferry signed a four-and-a-half-year professional contract with the club in January 2006. He was part of the team that won the Under-19 League and Cup double in 2006 and was among a number of players named, by coach Willie McStay, as likely to progress to the first team.

In July 2006, Ferry played for Scotland at the 2006 European Under-19 Championship. The Scottish team reached the final, in which Ferry played, but they lost to Spain.

Simon "Si" William Ferry (born 11 January 1988) is a Scottish semi-professional footballer and semi-professional sports broadcaster who plays for Peterhead.