In 1999 Street Roots replaced the “Burnside Cadillac” newspaper to become Portland's flagship publication addressing homelessness and poverty.
In 2000 Street Roots supported the creation of Dignity Village, Portland's only city-sanctioned homeless community that provides open-air alternative to shelters. .
In 2005 Managing Editor Joanne Zuhl was awarded the Steve Lowenstein Award, and Director Israel Bayer receives the Cecil M. Shumway Fund award for service to the poor and underprivileged in Portland. A feature in the Society for News Design calls Street Roots "one of the best, if not the best, street papers in the country."
In 2006, Street Roots and the North American Street Newspaper Association joined the International Network of Street Papers, a network that spans the globe with more than 70 newspapers and a combined circulation of 55 million.
In 2008, Street Roots Executive Director Israel bayer became the North American Street Newspaper Association Chairperson, helping build a network of strong papers throughout the U.S. and Canada. Portland City Commissioner Erik Sten said "Street Roots has changed the face of homelessness in Portland."
In 2009, Street Roots launched the Rose City Resource, a 104-page booklet that offers the most comprehensive list of services in the Portland region for people experiencing homelessness and poverty. Street Roots was awarded one of the best volunteer organizations by the Portland Trail Blazers.
In 2010: Street Roots joined the Society of Professional Journalists, earning three first place prizes in its first year. Israel Bayer was awarded the Skidmore Prize for being one of the best non-profit leaders in the city under the age of 35.
In 2011 Street Roots initiated an in-depth series' on Traumatic Brain Injuries and Asperger's Syndrome, respectively. It received the Veterans for Peace award for the newspaper's on-going coverage of veterans
In 2015 Streets Roots began “weekly” publication, after many years as a bi-weekly publication