He began coding the WikiWikiWeb in 1994, and installed it on c2.com (the website of his software consulting firm) on March 25, 1995, as an add-on to the Portland Pattern Repository.

Cunningham was a keynote speaker at the first three instances of the WikiSym conference series on wiki research and practice, and also at the Wikimedia Developer Summit 2017.

[9] Cunningham has also served as Director of R&D at Wyatt Software and as Principal Engineer in the Tektronix Computer Research Laboratory.

[3][10] On March 24, 2011 The Oregonian reported that Cunningham had departed AboutUs to join the Venice Beach-based CitizenGlobal, a startup working on crowd-sourced video content, as their chief technology officer and the Co-Creation Czar.

The most famous among these are the wiki and many ideas in the field of software design patterns, made popular by the Gang of Four (GoF).

[17][better source needed] When asked in a 2006 interview with internetnews.com whether he considered patenting the wiki concept, he explained that he thought the idea "just sounded like something that no one would want to pay money for.

Cunningham has contributed to the practice of object-oriented programming, in particular the use of pattern languages and (with Kent Beck) the class-responsibility-collaboration cards.

[22] Cunningham relativises his ownership of the law, calling it a "misquote that disproves itself by propagating through the internet" and by saying that he "never suggested asking questions by posting wrong answers".