Liberty League was founded in 1995 as the Upstate Collegiate Athletic Association (UCAA), consisting of the following schools:
- St. Lawrence
- William Smith
The schools in bold sponsored football, but only five would play in the conference. Hamilton was also a member of the New England Small College Athletic Conference (NESCAC) and chose to play football in that conference.
A five-member conference was not a problem until 1999, when the NCAA tournament expanded, which allowed for automatic qualifiers to the tournament but required a conference with at least seven members. In 2004 the UCAA changed its name to the Liberty League concurrent with three teams joining football as associate members of the conference, finally gaining an automatic qualifier. Membership has changed since then; the following are the current football members of the Liberty League:
- Buffalo State (associate member)
- St. Lawrence
|1995||Upstate Collegiate Athletic Association (UCAA) founded.
Football began with Hobart, RPI, Rochester, St. Lawrence and Union, all previously independent.
|2004||Conference changed its name to the Liberty League.
Coast Guard, Merchant Marine and WPI joined as associate members, all were previously in the Freedom Football Conference.
|2005||Coast Guard departed after the season for the New England Football Conference (NEFC, now Commonwealth Coast Football).|
|2007||Susquehanna joined as an associate member from the Middle Atlantic Conference (MAC).|
|2009||Susquehanna departed after the season for the Centennial Conference.|
|2012||Springfield joined as an associate member from the Empire 8.|
|2016||Merchant Marine, Springfield and WPI all departed after the season for the New England Women's and Men's Athletic Conference (NEWMAC).|
|2017||Ithaca joined as a full member from the Empire 8.|
|2019||Buffalo State joined as an associate member from the Empire 8.|
|2020||Season canceled due to COVID-19 pandemic.|