- In 1996, Commonwealth Shakespeare Company’s first production, A Midsummer Night’s Dream, won the Elliot Norton Award for Best Direction.
- An internship program for the development of the next generation of Shakespearean actors was launched in 1998 as part of the company’s educational outreach programming.
- The Wang Center for the Performing Arts (now Citi Performing Arts Center) formed a strategic alliance with CSC in 2003.
- Performances were moved in 2005 from the Parkman Bandstand area to the Parade Ground on the historic Boston Common to accommodate growing nightly crowds.
- Audience for the 20 performances of The Taming of the Shrew (2006) reached a record 100,000 patrons.
- Major supporters of Citi Performing Arts Center's public programming 2004 - 2008: Barr Foundation, The Boston Foundation, The Boston Globe, Boston Parks and Recreation, Carl and Ruth Shapiro Family Foundation, City of Boston, Greater Boston, Convention and Visitors Bureau, Fidelity, John Hancock Financial Services, Inc., Jane's Trust, Massachusetts Cultural Council, MOTT, National Endowment for the Arts, Poduska Family Foundation, Target Corporation
- In 2008 the relationship with Citi Performing Arts Center was re-engineered to establish a producing partnership while maintaining separate corporate structures and identities.
- In 2009, Commonwealth Shakespeare Company with the help of its Board and Friends reinstated itself as the sole enterprise behind Shakespeare on the Common and is back to producing independently!