Barnsley Born in
Rotherham, South Yorkshire, He made an instant impression, and played eleven matches in the next three months. In the 2005–06 season, he was picked to play for a "Football League XI", in a match against their Italian counterparts. He went back to being second choice at Barnsley, this time to
Nick Colgan and was an unused substitute in Barnsley's
play-off final win against
Swansea City. Because of this, he only made a few more league and cup appearances in which he again impressed, leading to trials at
Chelsea and
Wigan Athletic.
Crystal Palace Flinders' transfer fee from Barnsley to Palace was believed to be for £250,000 but with a potential to rise to £1 million depending on appearances. Flinders made his competitive debut for Palace in a
League Cup tie with
Notts County, playing the full match as Palace were beaten 2–1. This would be his last appearance before going on loan to
League One club
Gillingham, where he made his debut in a 2–1 away win against
Doncaster Rovers on 9 September 2006. His loan with Gillingham was extended for a second month, but this extended loan did not last its full spell. He returned to the Crystal Palace bench by 28 October. For the next match, a trip to
Sheffield Wednesday, Flinders made his league debut with The Eagles, while
Gábor Király was dropped to the bench for a match which ended in a 3–2 defeat. This was quickly followed by a match at
Loftus Road, against
Queens Park Rangers, which ended in a 4–2 loss, after which he was dropped, not returning until late December. On 20 February 2007, Flinders was sent out on loan again. He signed for Palace's rivals,
Brighton & Hove Albion, after their first choice goalkeeper
Michel Kuipers was injured. He made his Seagulls debut at his previous club Gillingham, a match which his new team won 1–0. Flinders was sent out on loan again in February 2008, this time to
Yeovil Town, after their first choice goalkeeper
Steve Mildenhall was injured. However, despite Yeovil signing him for further month loan period, on 27 March, Championship club
Blackpool signed him on loan until the end of the
season as competition for first-choice keeper,
Paul Rachubka. With Blackpool's next match being an away match at Crystal Palace he was not allowed to make his debut for the club until after that match. However, his loan period finished without him making an appearance for Blackpool. In August 2008, Flinders signed for
Scottish Premier League club
Falkirk on loan until January 2009, and he returned to Palace at the end of this spell. Flinders was released by Crystal Palace on 6 May 2009.
Hartlepool United in 2011 On 26 June 2009, Flinders signed for League One club
Hartlepool United. He played every minute of the
2009–10 season for Hartlepool in both league and cup, the next
season he was limited to 26 league appearances due to an injury in mid-September which ruled him out until February which saw Pools boss
Mick Wadsworth draft in
Blackburn Rovers goalkeeper
Jake Kean on loan to cover for Flinders. Flinders became the first ever goalkeeper to score a goal from open play for Hartlepool when his 94th-minute header against
AFC Bournemouth on 30 April 2011 gained a point for his employers on the last home match of the season. He nearly scored in consecutive home matches for the club when against
Walsall on 13 August 2011, when his 5th minute clearance from 70 yards bounced over Saddlers' keeper
Jimmy Walker only for striker
Colin Nish to tap in on the line for Nish's first Hartlepool goal. Flinders signed a new contract with the club in May 2011. Flinders was nominated for League One's Player of the Month for September 2011, along with Hartlepool manager Mick Wadsworth being nominated for Manager of the Month, after conceding only two goals in four matches which saw his team win all four matches. However, he was unsuccessful as
Preston North End striker
Neil Mellor won the accolade. In January 2013, Hartlepool manager
John Hughes revealed to the
Hartlepool Mail that clubs in the higher divisions were looking to sign Flinders with Hughes saying "I know there are a lot of clubs looking at big Scotty. It's no surprise others are looking at him and we're just grateful and thankful that he's in goal for Hartlepool. The way he conducts himself in his training and preparation and his values are first class." In April 2013, prior to Hartlepool's final home match of the season, Flinders was voted Player's Player, Supporter's Player and Away Player of the Year for the
2012–13 campaign. Twelve days later, it was announced that Flinders had won the
Hartlepool Mail SportsMail Player of the Year Award. After a 0–0 draw against
Portsmouth in December 2013, Flinders broke a club record for the most clean sheets in the league for Hartlepool. Flinders became the first ever Hartlepool goalkeeper to make 200 Football League appearances for the club after a 4–0 win against
Bristol Rovers in March 2014. In the
2014–15 season, Flinders captained Hartlepool to their 'great escape' from relegation to the
National League. Flinders played his last game for Hartlepool in a 3–3 draw against
Carlisle United.
York City in 2015 On 23 June 2015, Flinders signed for Hartlepool's
League Two rivals
York City on a one-year contract, with the option of a further year. He made his debut in the opening match of
2015–16, a 3–0 defeat away to
Wycombe Wanderers on 8 August 2015. He made 48 appearances in 2015–16, York had the second-poorest defensive record with 87 goals conceded; York exercised their option to extend his contract for
2016–17. On 23 August 2016, Flinders was suspended for five matches by
the Football Association (FA) after being found guilty of racial abuse during a match against
AFC Wimbledon on 19 March 2016. He was also fined £1,250 and ordered to attend an education course. In September 2016, the suspension was lifted by the club and Flinders returned to training, although he had lost his place in the team to new signing
Kyle Letheren. Shortly after, Flinders was found guilty of racial abuse by the FA regulatory commission, having told AFC Wimbledon player
Lyle Taylor that his wife "doesn't like your kind", after Taylor grabbed Flinders' testicles and goaded him. On 20 September 2016, Flinders joined York's National League rivals
Macclesfield Town on a 28-day loan until 18 October. He made his debut four days later when starting their 2–1 away win over
Guiseley, finishing the loan with five appearances. Flinders again lost his place in the York team in November 2016, and left the club by mutual consent on 5 January 2017.
Macclesfield Town On 6 January 2017, Flinders signed for Macclesfield Town permanently on a contract until the end of the 2016–17 season. He helped Macclesfield Town reach the
2017 FA Trophy Final but ended up on the losing side, suffering a 3–2 loss against
York City. He was released at the end of the
season.
Cheltenham Town Flinders signed for League Two club
Cheltenham Town on 31 August 2017. After a few months he agreed a new contract with the club that would keep him at Cheltenham until the summer of 2019. In May 2019 he signed another new contract which extended his stay until the summer of 2021. On 4 January 2020, he suffered a broken leg during a 3–0 home win over
Oldham Athletic. After nine months on the sidelines, he returned to the team in an
EFL Trophy group stage win over
Plymouth Argyle in October 2020. On 6 May 2022, Flinders was released by Cheltenham Town after not being offered a further contract.
Mansfield Town On 6 June 2022, Flinders agreed to join League Two side
Mansfield Town on an initial one-year deal upon the expiration of his contract with Cheltenham Town. On 28 January 2023, Flinders impressed on his League debut in a 4–1 win against
Doncaster Rovers. In May 2024, Flinders signed a new contract to keep him at the club for a further year. On 19 June 2025, the club announced he had left after failing to reach a new deal. ==International career==