| Date | Venue | Opponents | Score[1] | Competition | Raith Rovers scorer(s) | Match Report |
|---|
| 11 July 2009 | Stark's Park | Airdrie United | 2–0 | F | Williamson (2) | Raith Rovers Official Site |
| 14 July 2009 | Stark's Park | Norwich City | 0–1 | F | | Raith Rovers Official Site |
| 18 July 2009 | Ainslie Park | Hamilton Academical | 2–2 (1-4 on penalties) | Spartans Tournament | Williamson (2, 2nd pen) | Raith Rovers Official Site |
| 19 July 2009 | Ainslie Park | Blyth Spartans | 4–2 | Spartans Tournament | Bryce (2), Ferry, Walker | Raith Rovers Official Site |
| 21 July 2009 | Stark's Park | Hibernian | 1–0 (Match abandoned) | F | Williamson | Raith Rovers Official Site |
| 22 July 2009 | Olivebank Stadium | Musselburgh Athletic | 0–1 | F | | Raith Rovers Official Site |
| 25 July 2009 | Forthbank Stadium | Stirling Albion | 1–2 | SCC | Walker | Raith Rovers Official Site |
| 26 July 2009 | Duffus Park | Cupar Hearts | 7–3 | F | McKechnie (3), Mackie (2), Elder, Bryce | Raith Rovers Official Site |
| 28 July 2009 | Stark's Park | Kilmarnock | 1–1 | F | Bryce | Raith Rovers Official Site |
| 29 July 2009 | Peffermill | Tynecastle | 2–0 | F | Mackie, Beveridge | Raith Rovers Official Site |
| 1 August 2009 | Bayview Stadium | East Fife | 3–2 | SLC | Walker, Tadé, Williamson | Raith Rovers Official Site |
| 2 August 2009 | Muirhouse | Civil Service Strollers | 3–1 | F | Bryce, Mackie, Trialist | Raith Rovers Official Site |
| 5 August 2009 | Ferguson Park | Whitehill Welfare | 2–2 | F | Bryce, Trialist | The Scotsman (No official site reports from either side) |
| 8 August 2009 | Palmerston Park | Queen of the South | 1–1 | First Division | Walker | Raith Rovers Official Site |
| 15 August 2009 | Stark's Park | Dundee | 2–2 | First Division | Williamson, Ellis | Raith Rovers Official Site |
| 22 August 2009 | Victoria Park | Ross County | 1–0 | First Division | Hill | Raith Rovers Official Site |
| 26 August 2009 | East End Park | Dunfermline Athletic | 1–3 | SLC | | Raith Rovers Official Site |
| 29 August 2009 | East End Park | Dunfermline Athletic | 2–0 | First Division | Murray, Casalinuovo | Raith Rovers Official Site |
| 3 September 2009 | Central Park | Cowdenbeath | 1–1 (3-4 on penalties) | Fife Cup | Ferry | Raith Rovers Official Site |
| 12 September 2009 | Stark's Park | Partick Thistle | 1–1 | First Division | Casalinuovo | Raith Rovers Official Site |
| 19 September 2009 | Stark's Park | Greenock Morton | 3–0 | First Division | Tadé (2), Ferry | Raith Rovers Official Site |
| 26 September 2009 | Somerset Park | Ayr United | 0–1 | First Division | | Raith Rovers Official Site |
| 10 October 2009 | Excelsior Stadium | Airdrie United | 2–1 | First Division | Williamson, Davidson | Raith Rovers Official Site |
| 13 October 2009 | Stark's Park | Inverness CT | 0–1 | First Division | | Raith Rovers Official Site |
| 17 October 2009 | Stark's Park | Queen of the South | 1–0 | First Division | Russell | Raith Rovers Official Site |
| 24 October 2009 | Dens Park | Dundee | 1–2 | First Division | Smith | Raith Rovers Official Site |
| 31 October 2009 | Firhill Stadium | Partick Thistle | 2–1 | First Division | Wallace, Sloan | Raith Rovers Official Site |
| 7 November 2009 | Stark's Park | Dunfermline Athletic | 1–2 | First Division | Campbell | Raith Rovers Official Site |
| 14 November 2009 | Cappielow | Greenock Morton | 0–5 | First Division | | Raith Rovers Official Site |
| 21 November 2009 | Stark's Park | Ayr United | 0–0 | First Division | | Raith Rovers Official Site |
| 28 November 2009 | Stark's Park | Peterhead | 0–0 | SC | | Raith Rovers Official Site |
| 1 December 2009 | Balmoor | Peterhead | 4–1 | SC | D.Smith (2), K.Smith, Simmons | Raith Rovers Official Site |
| 12 December 2009 | Caledonian Stadium | Inverness CT | 0–1 | First Division | | Raith Rovers Official Site |
| 15 December 2009 | Stark's Park | Airdrie United | 1–1 | First Division | Amaya | Raith Rovers Official Site |
| 16 January 2010 | Stark's Park | Partick Thistle | 1–0 | First Division | K.Smith | Raith Rovers Official Site |
| 23 January 2010 | Stark's Park | Greenock Morton | 1–2 | First Division | | Raith Rovers Official Site |
| 25 January 2010 | Stark's Park | Airdrie United | 1–1 | SC | Smyth (o.g.) | Raith Rovers Official Site |
| 27 January 2010 | Excelsior Stadium | Airdrie United | 3–1 | SC | | Raith Rovers Official Site |
| 6 February 2010 | Stark's Park | Aberdeen | 1–1 | SC | Williamson | Raith Rovers Official Site |
| 13 February 2010 | Stark's Park | Inverness CT | 0–4 | First Division | | Raith Rovers Official Site |
| 16 February 2010 | Pittodrie Stadium | Aberdeen | 1–0 | SC | Tadé | Raith Rovers Official Site |
| 6 March 2010 | Victoria Park | Ross County | 0–1 | First Division | | Raith Rovers Official Site |
| 9 March 2010 | Stark's Park | Ross County | 2–1 | First Division | Walker, Tadé | Raith Rovers Official Site |
| 13 March 2010 | Dens Park | Dundee | 2–1 | SC | Simmons, Ellis | Raith Rovers Official Site |
| 16 March 2010 | East End Park | Dunfermline Athletic | 1–2 | First Division | Walker | Raith Rovers Official Site |
| 20 March 2010 | Stark's Park | Dunfermline Athletic | 1–2 | First Division | Tadé | Raith Rovers Official Site |
| 23 March 2010 | Cappielow | Greenock Morton | 1–1 | First Division | Murray | Raith Rovers Official Site |
| 27 March 2010 | Stark's Park | Ayr United | 1–1 | First Division | Simmons | Raith Rovers Official Site |
| 3 April 2010 | Caledonian Stadium | Inverness CT | 3–4 | First Division | Williamson, Tadé, Mole | Raith Rovers Official Site |
| 7 April 2010 | Somerset Park | Ayr United | 2–0 | First Division | Murray, Williamson | Raith Rovers Official Site |
| 11 April 2010 | Hampden Park | Dundee United | 0–2 | SC | | Raith Rovers Official Site |
| 14 April 2010 | Excelsior Stadium | Airdrie United | 0–3 | First Division | | Raith Rovers Official Site |
| 17 April 2010 | Palmerston Park | Queen of the South | 0–3 | First Division | | Raith Rovers Official Site |
| 19 April 2010 | Firhill Stadium | Partick Thistle | 0–0 | First Division | | Raith Rovers Official Site |
| 21 April 2010 | Stark's Park | Dundee | 1–0 | First Division | Hill | Raith Rovers Official Site |
| 24 April 2010 | Dens Park | Dundee | 0–2 | First Division | | Raith Rovers Official Site |
| 26 April 2010 | Stark's Park | Airdrie United | 0–1 | First Division | | Raith Rovers Official Site |
| 28 April 2010 | Stark's Park | Queen of the South | 0–0 | First Division | | Raith Rovers Official Site |
| 1 May 2010 | Stark's Park | Ross County | 4–1 | First Division | Armstrong, Russell (3) | Raith Rovers Official Site | |
