Boland joined the Wisconsin Army National Guard in 1956. He then began training at Fort Leonard Wood and Fort Sill. In 1959, Boland was commissioned an officer.
During the Berlin Crisis of 1961, Boland was assigned to the 32nd Infantry Division and stationed at Fort Lewis. In 1963, he was sent to Fort Rucker, where he began aviation training. After completing his training the following year, he was stationed in Hanau, Germany.
In 1966, Boland was deployed to serve in the Vietnam War. He flew the de Havilland Canada DHC-3 Otter in support of Special Forces operations. The following year, he returned to Fort Rucker to train future combat pilots. In 1969, Boland returned to Vietnam, assigned to the 101st Airborne Division. He assumed command of a Bell AH-1 Cobra unit. Afterwards, he again returned to Fort Rucker as an instructor.
After serving with the 1st Cavalry Division at Fort Hood, Boland attended the United States Army Command and General Staff College, graduating in 1975. In 1978, he became an aviation battalion commander with the 25th Infantry Division. He remained in that position until 1980, when he began attending the United States Army War College, graduating the following year. Afterwards, he was named Deputy Chief of Staff for Training of United States Army North. In 1985, Boland was assigned to the 3rd Infantry Division at Giebelstadt Army Airfield.
In 1988, Boland became garrison commander of Fort McCoy. During this time, he supported mobilization of units for deployment during the Gulf War. Boland retired in 1991 with the rank of colonel.
Awards he received during his career include the Legion of Merit, the Distinguished Flying Cross, Bronze Star Medal, the Purple Heart, the Meritorious Service Medal, the Air Medal, the Army Commendation Medal, Master Army Aviator Badge, the Presidential Unit Citation and the Vietnamese Gallantry Cross.
