Cleveland Women’s Sports (CWS) began in June 2018 as a round-table meeting with numerous local team representatives about challenges their organizations were facing. The initial teams included Burning River Roller Derby, Cleveland Comets Softball, Cleveland Crush Basketball, Cleveland Fusion Football and Cleveland Iron Maidens Rugby. This conversation expanded to identify ways that teams could work together to minimize financial and logistical burdens, which culminated in the first joint fundraiser of a 2019 Cleveland Women’s Sports calendar.

Monthly meetings continued through this time and Notorious CLE Ultimate Frisbee was added into the fold. In the spring of 2019, multiple teams participated in an All-Access Ticket to encourage fans to attend multiple teams’ events throughout their seasons. That summer, the teams hosted joint booths at the Pride in the CLE and Akron Pride festivals to aid in recruiting and spreading awareness.

In November 2019, CWS leaders, Elise Bigley and Barbara Anthony, were invited to speak about the organization at the Alliance for Social Workers in Sports (ASWIS) annual conference in Denver, Colorado. Around this time, the second calendar fundraiser began production and sales.

Cleveland Women’s Sports partnered with the Cleveland Monsters hockey team for a women’s sports night in March of 2020.

In the summer of 2020, the co-ed Cleveland Aquatic Team and Cyrano's Place Fencing Club joined the alliance.