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He signed a new one-year deal with Chester in June 2019 after completing a training regime with the club's strength and conditioning coach set by joint-managers Anthony Johnson and Bernard Morley. Roberts said that “They know I’m a madman, but it’s managing that madman.” He scored two goals in 25 appearances in the 2019–20 season, which was permanently suspended on 26 March due to the COVID-19 pandemic in England, with Chester in the play-offs in seventh place.

Roberts signed with National League North club Southport in July 2017, who were managed by former Floriana boss Alan Lewer. He scored four goals in 14 matches for the "Sandgrounders", before his contract was cancelled by mutual consent in December 2017. On 9 January 2018, he signed a short-term contract with his hometown club, Chester, who were playing in the National League. Mark Maguire, CEO of the "Seals", said that: "What happens next will be largely down to Gary and will either be seen as a stroke of genius or madness. It certainly won't be boring!". Roberts was sent off ten minutes into his debut in an FA Trophy loss at East Thurrock United, leaving him with a three-game suspension, though the club's Community Trust and Exiles supporters group stepped in to fund his wages for another month after the expiry of his initial contract. Chester were relegated at the end of the 2017–18 season, though Roberts said that departing manager Marcus Bignot was "one of the best, if not the best manager I've worked under". Roberts scored four goals in 34 National League North appearances in the 2018–19 season. He had aimed to help the club reach the play-offs after signing a one-year contract at the start of the campaign, though they ended up finishing two places and three points short of this target.

In January 2014, Roberts joined Welsh Premier League side Gap Connah's Quay. The "Nomads" finished tenth in 2013–14. He signed with Maltese Premier League side Mosta in January 2015. He returned to England later in the year to play for Witton Albion in the Northern Premier League Division One North, and left the club upon the expiry of his contract on 31 December. In June 2016, Roberts returned to the Welsh Premier League to play for Bangor City. He signed a contract extension four months later. The "Citizens" finished in fourth-place in 2016–17, and qualified for the UEFA Europa League after beating Cardiff Metropolitan University 1–0 in the play-off final; Roberts said "It means everything to the club [to be back in Europe]. We've worked hard as a unit, not just the players but all the staff". He credited the club with turning his life around and helping him to overcome his drink and gambling problems. However he left the club in July 2017 after having his contract cancelled; Bangor City made a statement to say "when a player states in the week leading up to a massive European game that he no longer wants to play for the club, we were left with no alternative other than to release him from his contract. We wish him well for the future, and hope that one day he realises what a massive opportunity he has given up."

Roberts signed an eighteen-month contract with Conference National club Mansfield Town on 1 January 2012. He made his debut on the same day, in a 2–2 draw at York City. He scored his first goals for the "Stags" on 28 January, in a 3–0 win over Ebbsfleet United at Stonebridge Road; after the game manager Paul Cox admitted that Roberts was too good a player for the Conference. Mansfield finished in third place at the end of the season, and qualified for the play-offs, losing to York City at the semi-final stage.

He played seven games at the start of the 2012–13 season, but was then sidelined with an ankle injury in September. After his recovery he disappointed in three league games and was dropped from the first team, with manager Paul Cox saying that Roberts would have to show "hunger and desire" to win back his place. However, he was sent off in a "humiliating" FA Trophy First Round defeat to Matlock Town. In January 2013, he joined Maltese Premier League side Floriana on loan until the end of the season. The "Greens" finished in the relegation grouping at the end of the 2012–13 season, but led the group after ten matches and remained in the top-flight. Roberts made 14 appearances for the club, and scored two goals in a 2–1 win over Rabat Ajax. In May 2013, Mansfield announced that they would not be offering Roberts a new contract in the summer.

He signed a new one-year deal with Vale in July 2011, after Micky Adams returned to the club as manager. After scoring five goals in his first nine games he admitted that "He [Adams] is the only manager that can control me so I think he gets the best out of me." However, on 19 September he was given a fourteen-day suspension by the club for 'a serious breach of club discipline', after he missed a day of training without any warning and then 'reported in unfit to carry out his duties' the following day; Adams said "I'm bitterly disappointed in him." He was also placed on the transfer list, as Adams stated "he's got a lot to do" before Roberts could think about a return to the first team. He made his return on 24 October, when Adams named him on the bench for a league clash with Bristol Rovers.

He received interest from Micky Adams' Port Vale, and joined the club on trial in July 2010. Acknowledging "it's a last-chance saloon", Roberts said "I've learnt just not to be a plonker for all my life." He joined the team on their July pre-season trip to Ireland, as Adams, already convinced of the player's talents, wanted to test Roberts' ability to stay away from his off-the-field demons. Roberts seemed to enjoy a good start to his Vale career, and after Adams' typically relentless pre-season fitness regime he claimed "I've turned the corner...I think I've got my act together but I've just got to keep living each day as it comes and as long as I wake up clean that's all that I need". He signed a six-month contract at the end of the month. He started the season well, maintaining discipline off the pitch, and his first team place on it, forging a midfield partnership with Anthony Griffith. As early as September he entered negotiations with the club to extend his contract, and Roberts quickly signed an extended contract to keep him at the club until the end of the season. However Micky Adams left the club in December 2010, and Roberts did not enjoy a happy relationship with new manager Jim Gannon. Gannon dropped him to the bench after Roberts admitted he did not enjoy playing in a more advanced position; Vale fans showed their support for the player by chanting his name throughout a 1–0 win over Rotherham. He then picked up a three-match ban after receiving a red card for violent conduct in a reserve match against Nottingham Forest. Gannon defended Roberts, believing the player was unlucky to be dismissed after he responded to a 'reckless' challenge by David Morgan by shoving Morgan to the ground. In March, speculation that he would leave Vale Park at the end of the season (or earlier) increased, as it was reported by BBC Radio Stoke that the club had informed the player he could leave on loan. However Gannon denied this on the club's website, stating that there was "no substance" to the report. In fact he went on to say "he has a huge part to play" in the club's promotion campaign. His teammates also showed their support for him by celebrating goals with Roberts' celebration style during his absence; club captain Marc Richards also dedicated his two goals against Shrewsbury Town to Roberts. Gannon's reign was quickly terminated, but Roberts still struggled to regain his form under caretaker-manager Mark Grew.

After he admitted to suffering from drink and gambling addictions he visited the Sporting Chance Clinic, determined to turn his life around. After his rehabilitation, he was originally offered a trial with League One side Brighton & Hove Albion, where he scored two goals in two reserve team games against Brentford and Leyton Orient. He left without an offer of a contract, but was offered another trial with League Two side Rotherham United, where he played in a reserves victory over Huddersfield Town. On 12 November, Roberts was offered a contract with the "Millers". Manager Ronnie Moore commented: "He's only 22 but has real talent... people say he comes with baggage but his attitude has been first class. I think he deserves a second chance." Later in the month Roberts signed a one-month contract. The following month the option to extend Roberts' Rotherham deal until the end of the 2009–10 season was taken. In his fifth appearance for Rotherham, a 4–2 win over Yorkshire rivals Bradford City, he scored his first goal for the club in 'sensational' fashion by finding the net with a free kick from fifty yards out. However, in April 2010 it was announced he had been sacked from Rotherham for breaking club discipline rules several times. The club did not divulge what the final breach was; though the "bitterly disappointed" manager said that while the player was "full of remorse" his teammates would not be "too sorry to see him go".

Roberts joined Yeovil Town on loan, initially for a four-month spell, in August 2008. After impressing during his loan spell at Huish Park, Roberts completed a permanent transfer to Yeovil for a nominal fee on 31 October 2008, with the deal officially going through on 1 January 2009. Roberts played 34 games for Yeovil during the 2008–09 season, scoring two goals. In his final game for Yeovil against Cheltenham Town he was sent-off. His girlfriend left him in May 2009, and Roberts was forced to move back in with his parents in Chester. On 5 August 2009, Roberts was suspended by Yeovil Town for a breach of club discipline and was released by mutual consent after reported drink and gambling problems, the final straw coming when he "turned up at a club-organised family fun day with the stench of alcohol on his breath". He later admitted his heart was not at the club, and that being alone in a hotel room away from his girlfriend and young son made it easier for him to turn to alcohol.

He scored the opening two goals of the 2007–08 season, in a 2–1 win over Brighton at the Alexandra Stadium. This led to him being named on the League One 'Team of the Week'. In 2007–08 his club once again had the best disciplinary record in the Football League. Once again Roberts received the only Crewe suspension and red card of the season, when he was given a second yellow card in a heavy defeat to Doncaster Rovers. He received four yellow cards in the season, all of which were for unsporting behaviour. His disciplinary problems off the pitch also first began to come to light, as he was left out of the squad for the March 2008 match with Nottingham Forest due to a "training ground incident". In June 2008 Roberts was placed on the transfer list by Crewe. Cardiff City were rumoured to be interested in signing Roberts, a fee of £150,000 was mentioned, but a transfer never materialised. Instead he trained alone all summer before being given another chance by Crewe boss Steve Holland. However, he failed to turn up at the club for pre-season training.

Roberts has attended the Sporting Chance Clinic for treatment of the drink and gambling problems which have dogged and severely damaged his football career; speaking of it all Roberts has said "I really can't believe what's happened to me. What's happened to my life." He has put his addiction problems down to "boredom". He also said that "I'm not one of these people who can have one drink and stop. I want another and another and another." His drink problems began after he developed a gambling habit in 2007. His addiction to betting on horse racing cost him £3,000 a month, and left him asking friends and family for money.

Roberts became a key player in Crewe's bid for promotion in the 2006–07 season, playing mostly as a midfielder. He made nineteen appearances during the season, scoring three goals – against Swansea City, Nottingham Forest and Yeovil Town. The first two goals came from the penalty spot, as he built his reputation as a solid penalty taker. He also received the first red card of his professional career in October 2006, in a defeat at Bristol City. He was dismissed for violent conduct after a challenge on Louis Carey, though the referee's decision was reported as 'harsh' and 'strange' by the Bristol City website. That red card was the only sending off, and subsequent suspension, of the season for Crewe, as the club was awarded the 'Bobby Moore Fair Play award for outstanding conduct and discipline throughout the season'.

On 20 May 2006, Roberts scored the winning goal as the England under-19's beat Northern Ireland under-19's 2–1 in a UEFA European Under-19 Championship elite qualification game in Belgium. He also played in the 2–1 defeat to Belgium, and 1–0 loss to Serbia and Montenegro; as England finished a disappointing last place in their group, failing to qualify for the tournament.

Roberts established himself in the Crewe first team in the 2005–06 season, making 33 Championship appearances and scoring two goals – against Millwall and Hull City. At the end of the season the club were relegated into League One, though Roberts was still given a new three-year contract, tying himself to the club until 2009.

He captained England under-18s in a goalless draw with Norway at Vale Park on 10 June 2005.

Roberts has a son, born around 2005 and a daughter born around 2013. He was born and raised in an area of Chester he describes as "one of the roughest council estates in the country"; he still resides there as of 2011.

He was in the England squad for the 2004 UEFA European Under-17 Championship. He played in all the matches, as England topped their group with a 2–0 win over Ukraine, a 3–1 win over Portugal, and a 1–0 victory over Austria. The team were eliminated at the semi-final stage by a Cesc Fàbregas penalty for Spain. He was sent off in the Third Place play-off against Portugal, as the team went on to lose in a penalty shootout.

He started his career with Crewe Alexandra in 2003, and made 133 league and cup appearances over the next five years. In 2008, he had a loan spell at Yeovil Town, before he joined the club permanently the following year. He signed with Rotherham United in November 2009, having impressed on trial, before he was released in summer 2010. Crewe, Yeovil and Rotherham all cited disciplinary problems as their reason for letting him go. He joined Port Vale in July 2010, having been handed a 'last chance' by manager Micky Adams. His contract was terminated in December 2011, again due to a disciplinary issue, and he signed with Mansfield Town. In January 2013 he joined Maltese club Floriana on loan. He spent a short period out of the game before he joined Welsh Premier League side Gap Connah's Quay in January 2014. He returned to Malta with Mosta in January 2015, coming back to England later in the year to play for Witton Albion. He joined Welsh club Bangor City in June 2016, and then switched to Southport in July 2017. He joined hometown club Chester six months later.

Roberts signed as a professional with Dario Gradi's Crewe Alexandra in 2004, on his 17th birthday, a few months after making his First Division debut for the club in a 3–1 win over Burnley on 26 December 2003. He later made a second appearance for the club against Wimbledon. He played a key part in the club's FA Youth Cup team which reached the semi-finals in 2004. However, he missed much of the 2004–05 season with a serious knee injury, only returning to first team action for games against Sheffield United and West Ham United in March 2005.

Gary Steven Roberts (born 2 February 1987) is an English footballer who plays for National League North club Chester. A deep-lying playmaker, he has been praised for his vision and ball distribution skills. However off the field he has struggled to control drink and gambling problems.