The Lakeland Conference was formed by seven small northwestern Wisconsin high schools in 1934: Cameron, Chetek, Clear Lake, New Auburn, Shell Lake, Turtle Lake, and Weyerhaeuser. Five of the original members of the Lakeland Conference were previously part of the Heart O'North Conference and left that conference due to growing size difference between the larger and smaller schools. All of the conference's original members were located in Barron, Chippewa, Polk, Rusk, and Washburn Counties. By the end of the decade, four new schools were added to the conference: Clayton in 1936, Bruce in 1937, Birchwood in 1938, and Prairie Farm in 1939. The next year, the Lakeland Conference split its eleven-member roster into Eastern and Western Sections:
Eastern Lakeland
Western Lakeland
Birchwood
Clayton
Bruce
Clear Lake
Cameron
Prairie Farm
Chetek
Shell Lake
New Auburn
Turtle Lake
Weyerhaeuser
Football was sponsored for the first time in 1938, with four members (Bruce, Cameron, Chetek and Clear Lake) participating first in seven-player football before switching to eight-player football in 1939. Aside from Weyerhaeuser's exit to become a charter member of the Flambeauland Conference in 1946 and their subsequent return five years later, conference membership remained consistent for sixteen years. In 1956, the Lakeland Conference welcomed three new members who were displaced when their conferences ceased operations in 1955: Balsam Lake and Centuria from the Northwest Border Conference and Tony from the Flambeauland Conference. This expansion brought membership to fourteen schools in two divisions:
Eastern Lakeland
Western Lakeland
Birchwood
Balsam Lake
Bruce
Centuria
Cameron
Clayton
Chetek
Clear Lake
New Auburn
Prairie Farm
Tony
Shell Lake
Weyerhaeuser
Turtle Lake
1957-1968
The Lakeland Conference lost three member schools in 1957. Chetek joined with larger schools in the Heart O'North Conference, and Balsam Lake and Centuria merged with Milltown of the Upper St. Croix Valley Conference to form the new Unity High School (not to be confused with the former Unity High School in Unity, Wisconsin). The new school inherited Milltown's conference membership, and the conference was left with eleven schools in two sections:
Eastern Lakeland
Western Lakeland
Birchwood
Clayton
Bruce
Clear Lake
Cameron
Prairie Farm
New Auburn
Shell Lake
Tony
Turtle Lake
Weyerhaeuser
Siren was accepted into the Lakeland Conference as its twelfth member in 1959 and took up residence in the Western section. Two years later, Tony would merge with Ingram-Glen Flora of the Flambeau League to form the new Flambeau High School, taking Tony's place in the Eastern Lakeland:
Eastern Lakeland
Western Lakeland
Birchwood
Clayton
Bruce
Clear Lake
Cameron
Prairie Farm
Flambeau
Shell Lake
New Auburn
Siren
Weyerhaeuser
Turtle Lake
In 1964, five Lakeland Conference members (Bruce, Clear Lake, Flambeau, Prairie Farm and Turtle Lake) made the transition to eleven-player football. Cameron joined them in 1966, and by 1967 the entire conference switched to eleven-player football, subdividing by enrollment size into two divisions.
1968-1994
In 1968, Winter joined the Lakeland Conference after leaving its former home in the Flambeau League, a conference which would break up two years later. Prentice would follow Winter's footsteps in 1970 after the disbandment of the Flambeau League. Lake Holcombe would also join the Eastern Lakeland in 1970, following a 5-year stint in the Cloverbelt. Cameron moved over to the Western section to accommodate the expansion:
Eastern Lakeland
Western Lakeland
Birchwood
Cameron
Bruce
Clayton
Flambeau
Clear Lake
Lake Holcombe
Prairie Farm
New Auburn
Shell Lake
Prentice
Siren
Weyerhaeuser
Turtle Lake
Winter
Prentice left the Lakeland Conference in 1978 to take up residence in its current home, the Marawood Conference. Two years later, Northwood High School in Minong joined the Western section of the conference after leaving the Indianhead Conference.
1994-2002
The conference would operate with fifteen members until 1994, when four schools displaced by the ending of the Upper St. Croix Valley Conference entered the Lakeland: Frederic, Grantsburg, Luck and Webster. The Lakeland Conference realigned itself into a three-division conference that year:
Central Lakeland
Eastern Lakeland
Western Lakeland
Cameron
Birchwood
Frederic
Clayton
Bruce
Grantsburg
Clear Lake
Flambeau
Luck
Prairie Farm
Lake Holcombe
Northwood
Shell Lake
New Auburn
Siren
Turtle Lake
Weyerhaeuser
Webster
Winter
This alignment would only remain in place for two years before going back to a two-division format in 1996. Cornell became the Lakeland Conference's twentieth member school when it moved over from the Cloverbelt Conference in 1998 and was aligned to the Eastern division:
Eastern Lakeland
Western Lakeland
Birchwood
Clayton
Bruce
Clear Lake
Cameron
Frederic
Cornell
Grantsburg
Flambeau
Luck
Lake Holcombe
Northwood
New Auburn
Shell Lake
Prairie Farm
Siren
Weyerhaeuser
Turtle Lake
Winter
Webster
2002-present
The Lakeland Conference returned to a three-division format in 2002 when it accepted two of the smaller schools from the Middle Border Conference as members (St. Croix Falls and Unity). Both schools joined the conference's Western division:
Central Lakeland
Eastern Lakeland
Western Lakeland
Cameron
Birchwood
Frederic
Clayton
Bruce
Grantsburg
Clear Lake
Cornell
Luck
Northwood
Flambeau
Siren
Prairie Farm
Lake Holcombe
St. Croix Falls
Shell Lake
New Auburn
Unity
Turtle Lake
Weyerhaeuser
Webster
Winter
This alignment would remain for nearly twenty years and was relatively stable in terms of membership. Weyerhaeuser merged with Chetek of the Heart O'North Conference in 2010 with the new school (Chetek-Weyerhaeuser) continuing Chetek's Heart O'North membership. For the 2012 football season, the Lakeland Conference subdivided into eight-player and eleven-player divisions, as eight members of the conference (Birchwood, Bruce, Luck, New Auburn, Northwood/Solon Springs, Prairie Farm, Siren and Winter) made the transition. Cameron and St. Croix Falls followed them to the Heart O'North in 2019 and 2021, respectively. The Lakeland Conference would also adopt its current two-division alignment that year. Membership decreased from nineteen to seventeen schools in 2025 when Clear Lake left for the Dunn-St. Croix Conference and Unity shifted to the Heart O'North Conference.