During Wilmore's tenure as a fleet Naval officer and pilot, Wilmore completed four operational deployments, flying the A-7E and F/A-18 aircraft from the decks of the aircraft carriers , , and (CVN-69). He has flown missions in support of Operations Desert Shield, Desert Storm and Southern Watch over the skies of Iraq, as well as missions over Bosnia in support of United States and NATO interests. Wilmore successfully completed 21 combat missions during Operation Desert Storm while operating from USS "John F. Kennedy". Wilmore's most recent operational deployment was aboard USS "Dwight D. Eisenhower" with the "Blue Blasters" of Strike Fighter Squadron 34 (VFA-34), an F/A-18 squadron based at Naval Air Station Oceana, Virginia.