Results of events posted here
| Event Date/Time | Team(s) | Location | Bus Depart Time | Details |
| Saturday, Aug 24 – 10am | Varsity | Madison Memorial | 9:15am | Scrimmage with Memorial, Arrowhead and Kettle Moraine |
| Tuesday, Aug 27 – 5:30pm | Varsity | Muskego | 3:00pm | Quad with Muskego, Burlington and Hamilton |
| Wednesday, Sept 4 – 5/6:30pm | V, JV Red, Fr | Madison LaFollette | 3:45pm | Conf match vs LaFollette |
| Thursday, Sept 5 – 5 & 7pm | JV White & Fr | Middleton | | Tri with Madison Edgewood, Madison Memorial & Beloit |
| Saturday, Sept 7 – 8:30am | Varsity | Brookfield East | 6:20am | 2019 Boys Volleyball Brookfield East Invite |
| Saturday, Sept 7 – 8:30am | JV Red | Kettle Moraine | 6:40am | _KMHS JV1 BOYS’ TOURNAMENT 2019 |
| Wednesday, Sept 11 – 4:30pm/6pm | V, JV White | Middleton | | Conf match vs Madison East |
| Saturday, Sept 14 – 8am | JV White | Marquette | 6:00am | Milwaukee Marquette Invite |
| Saturday, Sept 14 – 8:30am | JV Red | New Berlin | 6:20am | New Berlin Invite |
| Saturday, Sept 14 – 9am | Varsity | Wauwatosa East | 6:55am | Red Raider Invitational 2019.docx |
| Saturday, Sept 14 – 9am | Freshmen | Madison West | 8:00am | Madison West Invite |
| Wednesday, Sept 18 – 5/6:30pm | V, JV Red, JV White, Fr | Middleton | | Conf match vs Beloit – PARENT’S NIGHT |
| Thursday, Sept 19 – 5:30/7pm | V, JV Red, JV White | Marquette | 3:15pm | Non-Conf dual vs Milwaukee Marquette |
| Saturday, Sept 21 – 9am | JV Red | Kaukauna | 6:10am | Kaukauna Invite |
| Saturday, Sept 21 – 9am | JV White | Burlington | 6:30am | Burlington Invite |
| Tuesday, Sept 24 – 5/6:30pm | V, JV Red | Middleton | | Conf match vs Fort – Teacher Appreciation Night |
| Thursday, Sept 26 – 5 & 7pm | JV White, Fr | Middleton | | Tri with Hamilton and Edgewood |
| Saturday, Sept 28 – 9am | Varsity | Middleton | | Cardinal Invite |
| Wednesday, Oct 2 | V, JV White, Fr | Middleton | | Conf match vs Edgewood – Senior Night |
| Saturday, Oct 5 – 8:30am | Varsity | Whitefish Bay | TBD | WFB boys vb invite 2019 |
| Monday, Oct 7 – 5/6:30pm | V, JV Red, Fr | Madison Memorial | 4:15pm | Conf match vs Memorial |
| Saturday, Oct 12 – 9am | V, JV Red | Middleton | | 2019 Round Robin |
| Saturday, Oct 12 – 9am | JV White, Fr | Kimberly | 6:10am | 2019 Kimberly JV Invite 10.12.19 |
| Monday, Oct 14 – 5pm | JV Red, JV White, Fr | Middleton | | Matches with Fond du Lac |
| Wednesday, Oct 16 – 5/6:30pm | V, JV Red, Fr | Madison West | 4:05pm | Conf match with Madison West |
| Thursday, Oct 17 – 5pm | Fr, JV White | Middleton | | Big Eight Conference Tournament |
| Friday, Oct 18 – 5pm | Varstiy | Middleton | | Big Eight Conference Tournament |
| Monday, Oct 21 – 5pm | JV Red | TBD | | Big Eight Conference Tournament |
| Friday, Oct 25 – 7pm | Varsity | TBD | | WIAA Regionals |
| Tuesday, Oct 29 – 7pm | Varsity | TBD | | WIAA Sectional Semifinal |
| Saturday, Nov 2 | Varsity | Sun Prairie | | WIAA Sectional Final |
| Thursday – Saturday, Nov 7-9 | Varsity | Green Bay | | WIAA State Tournament |
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