| 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   (pen.), 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
 | 
Williamson   (pen.)
 | 
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
 | 
K.Smith   (pen.)
 | 
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
 | 
K.Smith, Tadé, Russell   (pen.)
 | 
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
 |