Stirling was a companion of the Maryland Commandery of the Military Order of the Loyal Legion of the United States as a veteran commissioned officer of the Civil War.

In June 1861, Stirling and several other midshipman, including Robley "Fighting Bob" Evans, future hero of the Spanish–American War, submitted letters of resignation, believing their loyalty was with the Confederacy.

Promoted to lieutenant commander on March 12, 1868, he was aboard the newly commissioned screw frigate USS Wampanoag during her brief initial deployment as flagship of the North Atlantic Squadron in 1868.

After a lengthy period on sick leave from 1873 to 1875, Stirling returned to duty aboard the receiving ship USS Worcester at the Norfolk Navy Yard in Portsmouth, Virginia, from 1875 to 1876.

Detaching from Lackawanna in 1881, he had a second tour of duty at the Washington Navy Yard from 1882 to 1884 before a sea assignment as commanding officer of the sloop-of-war USS Iroquois in the Pacific Squadron from 1884 to 1886.

[3][4] In May 1900, while commandant at San Juan, Captain Stirling rescued the Lloyd's agent there, a man named Butler who had jumped off the municipal pier that had caught fire.

[7] Stirling was commander-in-chief of the United States Asiatic Fleet from July 11, 1904, to March 23, 1905[8] before retiring from the Navy on May 6, 1905, at the mandatory age of 62.

When he was interviewed shortly after his retirement, Stirling recalled an incident early in his career when he was first lieutenant taking a ship into a New England harbor with some difficulty.

"[10] Stirling died on March 5, 1929, at his home, 11 East Chase Street, Baltimore, Maryland, survived by this wife, two sons and three daughters.

[11] Admiral Sterling was a member of the Military Order of the Loyal Legion of the United States and the Maryland Society of the Sons of the American Revolution.