After college, Richard C.B. Woods served as a commissioned officer in the U.S. Navy. He graduated, cum laude, from the University of Baltimore School of Law in December of 1979. While attending law school, he served as Associate Editor of the law review, published a case note (8 U.Balto.L.Rev. 598, 1979), was a member of the moot court championship team 1978-79, served as Secretary to the Student Bar Association 1977-78 and was inducted into the Heuisler Honor Society.

He joined the Bar in May of 1980, and went to work in the litigation section of Melnicove, Kaufman, Weiner & Smouse, P.A. He has practiced solo and as a partner at Marr, Swiss & Woods. He was also the managing partner of Swiss & Woods. He has extensive experience trying both civil and criminal cases in Maryland and in the United States District Court for the District of Maryland. His most often cited case is Shpak v. Schertle, 97 Md. App. 207 (1993) wherein he won a $750,000.00 jury verdict for a victim of sexual molestation. He has extensive experience as defense counsel and defended the British asbestos firm T&N, plc in the property damage case brought by the State of Maryland against numerous asbestos companies. He has successfully prosecuted a number of civil wrongful death cases recovering millions of dollars for his clients.

In addition to his civil litigation success, Richard C.B. Woods has won acquittals for numerous criminal defendants in Baltimore City and virtually every county in Maryland and in several surrounding jurisdictions. He has won acquittals for clients accused of murder, rape, assaults, drug offenses, armed robbery and felony theft. He is an active member of the Federal Trial Bar.