The first official Boys Basketball Conference Championship came in 1944, although the Lena basketball program had has success in prior years. 

Boys Basketball records from Lena date back to 1923-24 when the team went 2-1 under Coach Stienfeldt, beating Coleman 2-0 and 7-0, before falling to Oconto Falls 2-4.  In 1925 the boys beat Niagara 13-7 and it's noted in the record books that it was a 4 hour trip to Niagara that involved players having to push the car around every corner, and dig out of snow banks multiple times.  The boys compiled winning records multiple times including 16-4 in 1927 under Coach Greischar, 13-4 in 1939 under Coach Ernest Mitchell, and 16-2 in 1943 under Coach Kimball.  While these were all successful seasons, Boys Basketball didn't become an official conference sport in the M&O until 1944.

Early basketball records also contain some unique information about the district.  It's noted in the 1940-41 records that on November 15, 1940 Wildcats became the official symbol of Lena High School, winning a runoff election between "Wildcats" and "Rams".  

The 1944 Championship team finished the season with a 16-7 record, with the bulk of their losses coming to non-conference opponents Oconto (3 times), Marinette (2 times), and Bonduel.  The team tallied a school record 757 points on the year, led by Romie Kosnar (226), Gus Blahnik (195), Bob Schemberger (97), and Arvid McGuire (89).