Men's Tennis Schedule
| Date | Opponent | Location | Time | Result (s) |
| 9/9/08 | Central | Pella | 3:30 p.m. | Central 8, Simpson 1 |
| 9/19/08 | William Jewell | Indianola | 3:30 p.m. | William Jewell 8, Simpson 1 |
| 9/26/08 9/27/08 |
ITA Regional Tournament | St. Peter, Minn. | All Day | Tournament Website |
| 2/8/09 | Hastings College | Red Oak | 2 p.m. |
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| 2/12/09 | Buena Vista | Storm Lake | 1 p.m. | |
| 2/12/09 | Dordt | Storm Lake | 4 p.m. | |
| 2/14/09 | Dominican (Ill.) | Waverly | 12 p.m. | |
| 2/14/09 | Wartburg | Waverly | 3 p.m. | |
| 2/21/09 | Central | Pella | 9 a.m. | |
| 2/21/09 | Graceland | Pella | 12 p.m. | |
| 2/22/09 | Bethany Lutheran | Mankato, Minn. | 12 p.m. | |
| 2/28/09 | UW-La Crosse | Decorah | 2 p.m. | UW-La Crosse 9, Simpson 0 |
| 2/28/09 | Luther | Decorah | 5 p.m. | Luther 9, Simpson 0 |
| 3/6/09 | MSOE | Milwaukee, Wis. | 2 p.m. | MSOE 8, Simpson 1 |
| 3/25/09 | Rockford | Clinton | 1 p.m. | |
| 3/27/09 | Augustana (Ill.) | Indianola | 11 a.m. | Augustana 9 Simpson 0 |
| 3/27/09 | Dubuque | Indianola | 4 p.m. | Dubuque 8 Simpson 1 |
| 4/4/09 | Doane College | Crete, NE | 12:00 p.m. | |
| 4/7/09 | Central | Indianola | 3 p.m. | Central 7 Simpson 2 |
| 4/8/09 | Buena Vista | Indianola | 3 p.m. | Simpson 7 Buena Vista 2 |
| 4/11/09 | Cornell College | Indianola | 9 a.m. | Cornell 5 Simpson 4 |
| 4/11/09 | Morningside | Indianola | 3 p.m. | Simpson 6 Morningside 3 |
| 4/14/09 | Minnesota-Morris | Morris, MN | 3 p.m. | Simpson 8 Minn-Morris 1 |
| 4/17/09 | Loras | Indianola | 3:30 p.m. | Simpson 5 Loras 4 |
| 4/18/09 | Westminster | Fulton, Mo. | 11 a.m. | Canceled |
| 4/18/09 | Webster (Mo.) | Fulton, Mo. | 2 p.m. | Canceled |
| 4/21/09 | Wartburg | Indianola | 3:30 p.m. | Wartburg 8 Simpson 1 |
| 4/25/09 | Loras College | Dubuque | TBA | Canceled |
| 4/30/09 | IIAC Team Tournament | Iowa City, Dubuque, host | 8:30 a.m. | |
| 5/1/09-5/2/09 | IIAC Individual/Doubles Tournament | Cedar Rapids, Dubuque, host | All Day |