| Date | Opponent(s) | Result | Caption | Location | Transportation | |
|---|---|---|---|---|---|---|
| 4/1/21 |
vs
Pella
|
L 0-4 | Winterset High School | |||
| 4/5/21 |
vs
North Polk
|
W 3-2 | Winterset High School | |||
| 4/8/21 |
vs
Dallas Center-Grimes
|
L 0-10 | Winterset High School | |||
| 4/13/21 |
@
Perry
|
W 2-1 | Perry High School | |||
| 4/15/21 |
@
Des Moines North
|
L 1-8 | North High School | |||
| 4/17/21 |
vs
Oskaloosa
|
L 1-2 |
Winterset Tournament |
Winterset High School | ||
| 4/17/21 |
vs
Harlan Community
|
W 1-0 |
Winterset Tournament |
Winterset High School | ||
| 4/19/21 |
vs
Ballard
|
PPD |
Postponed |
Winterset High School | ||
| 4/23/21 |
@
Gilbert
|
L 0-4 | Gilbert High School | |||
| 4/27/21 |
@
Greene County
|
W 5-1 | Grand Junction Football Field | |||
| 4/29/21 |
@
ADM
|
L 1-5 | ADM High School | |||
| 5/4/21 |
@
Boone
|
W 6-1 | Goeppinger Field | |||
| 5/7/21 |
@
Indianola
|
W 1-0 |
Senior Night |
Indianola Stadium | ||
| 5/10/21 |
vs
Ballard
|
W 8-0 |
Varsity 1st @ 5:30PM |
Winterset High School | ||
| 5/11/21 |
vs
Bondurant-Farrar
|
L 0-5 | Winterset High School | |||
| 5/13/21 |
vs
Carroll
|
W 2-0 | Earlham High School | |||
| 5/17/21 |
vs
Carlisle
|
L 1-2 | Winterset High School | |||
| 5/20/21 |
vs
North Polk
|
W 1-0 |
Class 2A Substate 7 First Round |
Earlham High School | ||
| 5/24/21 |
vs
Carlisle
|
L 0-1 |
Class 2A Substate 7 Second Round |
Carlisle High School |
