Born at West Union Church near Waynesburg, Pennsylvania, Stockdale graduated from Jefferson College (now Washington & Jefferson College) in 1856 and received a master's degree in 1859.

[2][4] During the Civil War, he served in the Confederate States Army.

Enlisting as a private in the 16th Mississippi Infantry in 1861,[2] he was promoted to lieutenant, captain and major, and served as regimental adjutant.

[5][6] After the war Stockdale resumed the practice of law in Summit, Mississippi.

[8][9][10][11] In 1896 Stockdale was appointed by Governor Anselm J. McLaurin to fill a vacancy as a justice of the Mississippi Supreme Court and he served until 1897.