| Thu, Aug 28 | Shorewood Early Season Invite | Kern Park | Milwaukee, WI | | | |
| Sat, Aug 30 | Jamie Block Memorial Invitational | West Bend HS | West Bend, WI | | | |
| Sat, Sep 6 | Racine Horlick Rebel Invitational | Dannehl XC Course, Univ. of Wisconsin Parkside | Kenosha, WI | | | |
| Sat, Sep 13 | Retro Metro Meet | Washington Park | Milwaukee, WI | | | |
| Sat, Sep 13 | Forest Park Cross Country Festival | Forest Park | St. Louis, MO | 8:50 AM | | |
| Sat, Sep 20 | Marquette Invitational | Washington Park | Milwaukee, WI | 10:00 AM | | |
| Sat, Sep 27 | Roy Griak Invitational | Les Bolstadt Golf Course | Falcon Heights, MN | 3:05 PM | | |
| Sat, Oct 4 | Eagle Invitational | Dannehl XC Course, Univ. of Wisconsin Parkside | Kenosha, WI | | | |
| Fri, Oct 10 | Viking Invitational | McCarty Park | Milwaukee, WI | 3:30 PM | | |
| Sat, Oct 18 | Greater Metro Conference Championships | Mitchell Park | Brookfield, WI | 9:45 AM | | |
| Sat, Oct 25 | WIAA Division 1 Sectional 8 | Mitchell Park | Brookfield, WI | | | |
| Sat, Nov 1 | WIAA Division 1 State Championships | Ridges Golf Course | Wisconsin Rapids, WI | | | |
| Sat, Nov 29 | 2014 Footlocker Midwest Regionals | Dannehl XC Course, Univ. of Wisconsin Parkside | Kenosha, WI | | | |
