Source: SWWAL.org
| Time | Event | Location |
|---|---|---|
| Thursday, Dec 12, 2019 | ||
| 4:30PM | Middle School Meet vs. Mineral Point Middle School vs. Fennimore, Prairie du Chien MS | Fennimore High School |
| Monday, Jan 13, 2020 | ||
| 4:00PM | Middle School Invitational vs. Platteville Middle School, Cuba City Middle School, Darlington, Dodgeville, Iowa-Grant, Lancaster | Belmont High School |
| Tuesday, Jan 21, 2020 | ||
| 4:00PM | Middle School Invitational vs. Dodgeville, Cuba City, Darlington, Iowa-Grant, Lancaster, Platteville | Dodgeville High School |
| Thursday, Jan 23, 2020 | ||
| 4:00PM | Middle School Invitational vs. Iowa-Grant, Cuba City Middle School, Darlington, Dodgeville, Lancaster, Platteville Middle School | Iowa-Grant Elementary/Middle School |
| Tuesday, Jan 28, 2020 | ||
| 4:00PM | Middle School Invitational vs. Cuba City Middle School, Platteville Middle School, Darlington, Lancaster, Iowa-Grant | Cuba City High School/Middle School |
| Tuesday, Feb 11, 2020 | ||
| 4:00PM | Middle School Invitational vs. Multiple Schools | Mineral Point MS/HS |
| Thursday, Feb 13, 2020 | ||
| 4:00PM | Middle School Invitational vs. Darlington, Cuba City Middle School, Dodgeville, Iowa-Grant, Lancaster, Platteville Middle School | Darlington High School |
| Monday, Feb 17, 2020 | ||
| 4:00PM | Middle School Invitational vs. Cuba City Middle School, Platteville Middle School, Darlington, Lancaster, Iowa-Grant | Cuba City High School/Middle School |
| Thursday, Feb 20, 2020 | ||
| 4:00PM | Middle School Invitational vs. Lancaster, Cuba City Middle School, Darlington, Dodgeville, Iowa-Grant, Platteville Middle School Bus to leave at 2:50pm. Wrestlers to leave class at 2:40pm | Lancaster High School |