In 2006, the Woodland Conference welcomed four schools displaced by the cessation of the Parkland Conference: Brown Deer, Pewaukee, Shorewood and St. Francis.[7] To accommodate the expansion from eight to twelve members, the Woodland Conference subdivided along geographic lines:
North Division
South Division
Brown Deer
Cudahy
New Berlin Eisenhower
Greendale
New Berlin West
Greenfield
Pewaukee
St. Francis
Shorewood
Thomas More
Wauwatosa West
Whitnall
In 2009, South Milwaukee returned to the Woodland Conference after being dissatisfied by the competitive imbalance they experienced as members of the Southeast Conference.[8] The conference realigned again, with larger schools in the conference comprising the Black Division and smaller ones in the Blue Division:
Black Division
Blue Division
Greendale
Brown Deer
Greenfield
Cudahy
New Berlin Eisenhower
New Berlin West
South Milwaukee
Pewaukee
Wauwatosa West
Shorewood
Whtnall
St. Francis
Thomas More
After three years of this arrangement, the Woodland Conference realigned by geography into East and West Divisions in 2012. Pius XI also joined that year after leaving the Classic 8 Conference, replacing Thomas More after they joined the new Metro Classic Conference:[9]
St. Francis left the Woodland Conference in 2014 to join with smaller schools in the Midwest Classic Conference.[10] In 2017, the Woodland Conference lost Wauwatosa West to the Greater Metro Conference while accepting two of its former members (Milwaukee Lutheran and West Allis Central).[11]Wisconsin Lutheran also joined the Woodland Conference after the dissolution of their longtime home, the Wisconsin Little Ten Conference.[12] Milwaukee Lutheran became members of the East Division, and West Allis Central and Wisconsin Lutheran joined the West Division:
East Division
West Division
Brown Deer
Greendale
Cudahy
New Berlin Eisenhower
Greenfield
New Berlin West
Milwaukee Lutheran
Pewaukee
Shorewood
Pius XI
South Milwaukee
West Allis Central
Whitnall
Wisconsin Lutheran
The Woodland Conference will be expanding its membership roster to sixteen schools in 2025, accepting Waukesha North and Waukesha South from the Classic 8 Conference.[13] As of April 2025, an updated divisional alignment has not been announced.
In February 2019, in conjunction with the Wisconsin Football Coaches Association, the WIAA released a sweeping football-only realignment for Wisconsin to commence with the 2020 football season and run on a two-year cycle.[14] The eight-member conference originally referred to as the Woodland East featured Cudahy, Grafton, Greendale, Greenfield, Shorewood/Messmer, South Milwaukee, Whitnall and Wisconsin Lutheran as its original members.[15] All members with the exception of Grafton (whose primary affiliation is with the North Shore Conference) were full members of the Woodland Conference. Another conference that was first called the Woodland West changed its name to the Parkland Conference before competition began, reviving a name previously used for an all-sport conference from 1963 to 2006.[15] Membership remained intact for the first four seasons of play before changes were made for the 2024-2025 cycle. Cudahy was moved to the large-schools division of the Midwest Classic Conference, with full Woodland members Milwaukee Lutheran moving over from the Parkland Conference as their replacement.[16] For the 2026-2027 realignment cycle, the Woodland Conference will be losing three members: Grafton (Glacier Trails), Shorewood/Messmer (Midwest Classic) and Wisconsin Lutheran (North Shore). They will be replaced by the two high schools in West Allis, with Nathan Hale joining from the Greater Metro Conference and West Allis Central moving over from the Parkland Conference. Along with the Parkland Conference, the Woodland Conference will have seven schools each and play one mandatory crossover game per school.[17]
