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In his 18-year-long playing career, Crainey has also previously played for Celtic, Southampton, Leeds United, and Wigan Athletic and Fleetwood Town. He joined AFC Fylde in December 2015 for a brief spell. He is currently Fleetwood Town U16 Academy Coach.

Crainey was named in the Championship "Team of the Week", along with teammates Matthew Gilks and Marcel Seip, following his performance in Blackpool's 0–0 draw with Swansea City on 24 October at the Liberty Stadium.

Crainey signed a one-year deal with Wigan Athletic in June 2013. He left the club at the end of June 2014 when his contract expired. He then signed for Fleetwood Town. After leaving Fleetwood, Crainey trained with Barnsley before signing for National League North club AFC Fylde in December 2015 for a short spell.

On 22 January 2011, in a home defeat to Sunderland, Crainey suffered an ankle injury that saw him miss part of Blackpool's debut season in the Premier League. With Blackpool relegated back to the Championship, Crainey put pen to paper on a new two-year contract, Blackpool putting in a 'big offer' to help Crainey snub the interest of Premier League side Wigan Athletic.

On 26 November 2011, Crainey scored his second League goal for Blackpool in a draw against Birmingham City at Bloomfield Road. On 11 February 2012, Crainey scored his third League goal for Blackpool in a draw against Portsmouth with a free kick into the top right hand corner. At the end of the 2012–13 season, Crainey rejected a new contract from Blackpool.

On 16 November 2010 Crainey made a return to the Scotland set up under Craig Levein for a friendly against the Faroe Islands at Pittodrie to claim his seventh cap.

In June 2008 newspaper reports linked Crainey with a £250,000 move to fellow Championship club Burnley, but he instead signed a new contract with Blackpool. He missed the start of the 2008–09 season with a groin injury and Blackpool brought in Mohammed Camara on loan to cover for him. On 9 September the club confirmed that Crainey had undergone an operation the day before which would keep him out of action for a further four to six weeks. He made his comeback on 24 January 2009 as an 87th-minute substitute in a 2–0 win over Birmingham City at Bloomfield Road. That season he made a total of 17 appearances.

Crainey's recovery coincided with the return to fitness of loan player Robbie Elliott who was regarded as Dennis Wise's first choice left-back. Elliott featured on the bench for the game against Leicester City on 13 March 2007, in his first outing since returning from injury, but Crainey was not even included in the squad as Wise chose to start Armando Sá in that role. His last appearance was on 30 January 2007, in a 2–1 win over Hull City. Crainey was eventually released at the end of his Leeds contract on 15 May 2007 as the Whites were relegated to League One.

On 9 July 2007, Crainey signed for Blackpool in a one-year deal with an option for a further year. On 13 August 2007, he was named in the Press Association's Championship "Team of the Week". Crainey scored his first-ever league goal on 19 September 2007, in a 2–2 draw with Bryan Robson's Sheffield United at Bloomfield Road. On 3 December 2007, he was again named in the Press Association's Championship "Team of the Week". Crainey was also named in the Press Association's Championship "Team of the Week" on 4 February 2008. He made a total of 43 appearances (scoring one League goal) in the 2007–08 season as the Seasiders finished nineteenth in the Championship, the club's highest-place finish in the Football League in 27 years.

Crainey was a regular at the start of the 2006–07 campaign under former manager Kevin Blackwell, but played less following Blackwell's departure on 20 September 2006. Crainey featured in the heavy defeats that quickly ended John Carver's hopes of becoming the permanent Leeds manager. When new boss Dennis Wise took over, he dropped Crainey in favour of Eddie Lewis and, later, other options at left back. Crainey later regained his place, but then was dropped again before suffering an injury.

a. Two league play-off appearances for Leeds United in 2006 (included in 2005–06 total) b. Three league play-off appearances for Blackpool in 2010 (included in 2009–10 total)

Crainey started the 2003–04 season with Celtic, but on 6 February 2004 he moved to England when he signed for Premier League side Southampton. He made his debut four days later as the Saints lost 2–0 away to Arsenal. However, he was to make a total of just five Premier League appearances for Southampton.

On 6 August 2004, he joined Football League Championship side Leeds United, initially on loan before the move was made permanent four days later for a fee of £200,000. This was Leeds United's first cash signing since relegation from the Premier League in May 2004. He made his debut on 14 August in a 0–0 draw with Wolverhampton Wanderers at Molineux. He made a total of 11 appearances in the 2004–05 season. The following season he played a total of 30 games as Leeds United reached the Play-offs. However, Crainey was sent off in the 68th minute in the second leg of the semi-final, as the Whites beat Preston North End to reach the final, which they then lost 3–0 to Watford.

Crainey has been capped at under-21 and full level by Scotland. He made his full debut on 27 March 2002 as Scotland lost a friendly 5–0 to France at the Stade de France in Paris. He made a total of four appearances for Scotland in 2002, playing in the 1–2 friendly defeat to Nigeria at Pittodrie Stadium, Aberdeen on 17 April and another friendly defeat on 21 August, 0–1 to Denmark at Hampden Park, Glasgow. He then made his competitive debut in the UEFA Euro 2004 qualifying Group 5 2–2 draw with the Faroe Islands at Svangaskarð, Toftir on 7 September. His next international appearances came in 2004 in two more friendly defeats. On 31 March, 1–2 to Romania at Hampden Park and 0–1 to Denmark on 28 April at Parken Stadium, Copenhagen.

Born in Glasgow, Crainey started his professional career with Celtic in 1997. He made a total of 58 appearances for the Hoops. He scored one goal when Celtic beat Hearts 5–2 in the quarter-final of the 2000–01 Scottish League Cup. On 18 March 2001 he helped Celtic win the League Cup at Hampden Park when they beat Kilmarnock 3–0 in the Final. He then made 15 appearances as Celtic won the 2001–02 Scottish Premier League championship.

Stephen Daniel Crainey (born 22 June 1981) is a Scottish former professional footballer. A left back, he made 319 appearances in the Premier League and Football League, including 214 for Blackpool.