Crawford started his career with Raith Rovers, with whom he won the 1994 Scottish League Cup Final and played in the UEFA Cup. This earned him a move to English football with Millwall, but Crawford returned to Scotland after just one year. He had a mixed spell with Hibernian, suffering relegation but then winning promotion. Crawford then had the most productive spell of his career with Dunfermline Athletic, during which time he became a Scotland regular, amassing 25 caps in total. Crawford played in Scottish Cup Finals for both Dunfermline and Dundee United in the mid-2000s, losing both to Celtic. Crawford's stint with Dundee United came after a short-lived return to English football with Plymouth Argyle.
After short spells with Aberdeen and Dunfermline Athletic, Crawford signed for lower division club East Fife in 2008. He served East Fife as player/manager for just over a year before resigning as manager in October 2010.  In October 2011 Stevie was appointed assistant manager of Falkirk.
Crawford, who plays as a striker, began his career with Raith Rovers in 1992. Raith beat Celtic in a penalty shootout in the 1994 Scottish League Cup Final. Raith also played in the UEFA Cup against Bayern Munich.
After the 1995–96 season, Crawford moved on to Millwall, where he spent a single season and scored 11 goals. Hibernian signed Crawford in 1997, but were relegated from the top division before winning promotion back to the Scottish Premier League in 1999. Crawford moved to Dunfermline Athletic on loan for the 1999–2000 season, scoring 16 goals in 25 games.
Crawford signed for the Fife side permanently in July 2000 after a successful loan in the previous season. His first goal for the Pars came on 12 August 2000 against St Johnstone.  Crawford was Dunfermline's top scorer in his first season at East End Park, scoring 9 goals in 37 league matches. The next season was just as successful for Crawford in goalscoring terms and his goals elevated Dunfermline to finishing sixth in the league. His goal in the final game of the season against Rangers earned his side a 1–1 draw.  The 2002–03 season was perhaps Crawford's best season with the Pars. The third game of the season saw him score a hat-trick against Dundee  leading to him challenging for top scorer of the season with 19 goals in 35 games. Crawford's goals again helped the Pars move up the league, helping them finish fifth overall.
His final season at Dunfermline was the club most successful season in a number of years, which saw them finish 4th thanks to Crawford's 13 goals. This not only saw his side qualify for the UEFA Cup, but he also helped the Pars reach the 2004 Scottish Cup Final, which they lost 3–1 to Celtic. It was at this time that Crawford decided he wanted to leave Dunfermline to sign for a club in England.
Plymouth and Dundee United
Crawford signed for Football League Championship side Plymouth Argyle in 2004.  He failed to settle in England due to his lack of goals and his homesickness. After only six months he returned to Scotland, signing with Dundee United for a £80,000 fee.  His time at Tannadice was equally short-lived, although he did earn another Scottish Cup runners-up medal, as United lost the 2005 Scottish Cup Final to Celtic.
Aberdeen and return to Dunfermline
After joining Aberdeen at the start of the 2005–06 season, Crawford returned to Dunfermline in August 2006, despite being a regular starter at Pittodrie and among the top league scorers at the time. He signed a two-year deal with his hometown team  but failed to be as productive as he had been in his first spell with Dunfermline, scoring only 8 goals in two seasons. In April 2008, Crawford was told he would not be offered a new contract and was free to find a new club. 
Over the course of his career Crawford won 25 caps for Scotland, scoring 4 goals.  He made his debut (and scored) in a Kirin Cup tie in 1995, but did not make another appearance until 2001.  Crawford played regularly under the management of Berti Vogts.
It was reported in July 2008 that Crawford had turned down a move to the English Championship in favour of continuing his football in Scotland.  Crawford signed a two-year-deal with Scottish Second Division side East Fife a few days later.   After David Baikie resigned as manager on 14 April 2009, Crawford became caretaker player/manager,   and he was given the job on a permanent basis later that month.  After just over a year as manager, Crawford resigned as manager of East Fife, but remained with the club as a registered player.  
Crawford was appointed assistant manager of Falkirk in October 2011.  He moved to a similar position at Hearts in May 2014, working with Robbie Neilson.  Neilson and Crawford both moved to English League One side Milton Keynes Dons in December 2016. 
- Raith Rovers
- Scottish First Division
- Winner – 1998–99
- Dunfermline Athletic
- Dundee United
- Scottish Cup
- Runner-up – 2004–05
- Scottish First Division Player of the Year
|Scotland national team |
- Scores and results list Scotland's goal tally first.
|1||24 May 1995||Toyama Park Stadium, Toyama||Ecuador||2–1||2–1||Kirin Cup|
|2||15 October 2002||Easter Road, Edinburgh||Canada||1–1||3–1||Friendly match|
|3||15 October 2002||Easter Road, Edinburgh||Canada||3–1||3–1||Friendly match|
|4||27 May 2003||Tynecastle Stadium, Edinburgh||New Zealand||1–0||1–1||Friendly match|