| Date | Opponent | Location | JV Result | Varsity Result |
| 12/2/08 |
Spring Valley |
Elmwood |
L
31-35 |
W 59-58 |
| 12/5/08 |
St. Croix Central |
Hammond |
L
42-51 |
W 50-38 |
| 12/11/08 |
Glenwood City |
Glenwood City |
W
34-33 |
L
49-60 |
| 12/13/08 |
Mondovi |
Elmwood (1:00) |
L 36-51 |
L 54-57 |
| 12/19/08 |
Blair-Taylor |
Elmwood |
L
32-68 |
L 47-76 |
| 1/3/09 |
Gilmanton |
Gilmanton (1:00) |
W 56-41 |
L 56-62 |
| 1/6/09 |
Elk Mound |
Elk Mound |
L
35-54 |
L 35-51 |
| 1/9/09 |
Plum City |
Plum City |
L
32-69 |
L 44-71 |
| 1/17/09 |
Colfax |
Elmwood (1:00) |
L 18-69 |
L 45-61 |
| 1/20/09 |
Boyceville |
Boyceville |
L
30-57 |
W 54-48 |
| 1/23/09 |
Spring Valley |
Spring Valley |
L
22-38 |
L
43-68 |
| 1/27/09 |
Pepin |
Elmwood |
W 44-32 |
W 46-41 |
| 1/29/09 |
St. Croix Central |
Elmwood |
L
18-54 |
W 55-48 |
| 2/3/09 |
Glenwood
City |
Elmwood |
W
36-21 |
L 40-42 |
| 2/6/09 |
Mondovi |
Mondovi |
L 25-55 |
L 40-64 |
| 2/9/09 |
Elk Mound |
Elmwood |
L 37-67 |
L 48-50 |
| 2/12/09 |
Plum City |
Elmwood |
L 33-60 |
W 58-44 |
| 2/17/09 |
Pepin |
Pepin |
W 35-27 |
L 44-48 (OT) |
| 2/20/09 |
Colfax |
Colfax |
L 21-50 |
L 70-75 |
| 2/27/09 |
Boyceville |
Elmwood |
L 32-45 |
W 59-52 |
| 3/3/09 |
Alma |
Alma
(7:00 PM) |
- |
L 50-53 |