| Event Date/Time | Team(s) | Location | Bus Depart Time | Details |
| Sat, Aug 26 9:00am |
Varsity | Middleton | Scrimmage | |
| Wed, Aug 30 5:00pm |
Frosh, JV | TRI vs. Beloit & Madison West (JV)/Madison Memorial (FR) | ||
| Tue, Sep 5 5pm/6:30pm |
Frosh, JV, Varsity | at Beloit Memorial | 3:05pm | |
| Sat, Sep 9 | Varsity | at Racine Invite | 6:05am | Tournament information |
| Sat, Sep 9 | JV | at Kettle Moraine Invite | 7:10am | Tournament information |
| Tue, Sep 12 6:30pm |
Varsity | at Madison East | 5:20pm | |
| Sat, Sep 16 | Varsity | at Tosa East Invite | 6:45am | Tournament Information |
| Sat, Sep 16 | JV | at Burlington Invite | 6:30am | Tournament Information |
| Sat, Sep 16 | Frosh | at Marquette Invite | 6:15am | Tournament Information |
| Mon, Sep 18 | Frosh | at Arrowhead Quad | 3:15pm | Tournament Information |
| Wed, Sep 20 5pm |
Frosh, JV | TRI vs. Madison West & Madison LaFollette (JV)/Madison Memorial (FR) | ||
| Mon, Sep 25 4:30pm |
Frosh | Muskego Quad | 2:15pm | |
| Tue, Sep 26 5pm/6:30pm |
JV, Varsity | vs. Fort Atkinson | ||
| Fri, Sep 29 6:00pm |
Varsity | vs. Franklin | ||
| Sat, Sep 30 9:00am |
Varsity | Cardinal Invite | Tournament Information | |
| Mon, Oct 2 | Frosh | at Kettle Moraine Invite | 2:15pm | Tournament Information |
| Wed, Oct 4 5pm/6:30pm |
Frosh, JV, Varsity | vs. Madison Memorial (Parent’s Night) | ||
| Fri, Oct 6 5:00pm |
Varsity | at Germantown | 2:25pm | |
| Sat, Oct 7 8:30am |
Varsity | at Whitefish Bay Invite | Tournament Information | |
| Mon, Oct 9 5pm |
JV | Quad vs. Mad Memorial, Kenosha Bradford & Greendale | ||
| Thu, Oct 12 | Frosh, JV, Varsity | at Madison West | 4:00pm | |
| Sat, Oct 14 9am |
JV, Varsity | Middleton Round Robin | Tournament Information | |
| Tue, Oct 17 5pm/6:30pm |
JV, Varsity | vs. Madison LaFollette (Senior Night) | ||
| Fri, Oct 20 5:00pm |
Frosh | Conference Tourney at Beloit | 2:50pm | Tournament Information |
| Sat, Oct 21 8:30am |
Varsity | Conference Tourney at Madison East | 7:20am | Tournament Information |
| Mon, Oct 23 5:00pm |
JV | Conference Tourney at Madison Memorial | 4:05pm | |
| Wed, Oct 25 5pm/6:30pm |
JV, Varsity | at Muskego | 2:40pm | |
| Fri, Oct 27 | Varsity | Regionals | ||
| Tue, Oct 31 | Varsity | Sectionals | ||
| Thu, Nov 2 | Varsity Sectional at Middleton | |||
| Fri, Nov 10 5:30pm |
State at Wisc. Lutheran College | |||
| Sat, Nov 11 | State at Wisc. Lutheran College |
Middleton Boys Volleyball 