Dennis Roberts military career began with his enlistment in 1968 at age 1g with the united States Marine corps- He received an Honorable Discharge in 1970. His service included one year overseas duty with the Third Marine Division.
He enlisted in the Florida National Guard with the 153rd Engineer company in Lake city in 1977. He received his commission as a 2nd Lieutenant upon completion of officer candidate schoot in 1978. He graduated from the U.S. Army Judge Advocate Generals School in 1985 and was certified as a member of the JAG corps. He retired at the rank of Lieutenant Colonel and last served as Command Staff Judge Advocate for the 32nd Army Air Missile Defense command in Orlando.
Roberts was recognized nationally in 1999 when he was selected as the "Outstanding Senior National Guard Attorney" by the Judge Advocates Association of Washington, D.C. He also received the "Burton Award of Excellence" by the Florida Bar in 1994 as the outstanding military attorney in the state.
ln December 2006, Roberts was awarded the Florida Cross, the highest award given by the Florida National Guard, and the U.S. Army Legion of Merit which is the second highest non-combat award given by the U.S. Army. The criteria for both awards requires exceptional and meritorious conduct by a key individual over a significant amount of time above and beyond the performance of expected duties.