Citation:

The Distinguished Service Cross is presented to Frank C. Bolles, Second Lieutenant, U.S. Army, for extraordinary heroism in action during the attack on Jaro, Panay, Philippine Islands, February 12, 1899.

Second Lieutenant Bolles exhibited conspicuous bravery and skill in handling his detachment and directing the fire of his piece. Even after he was seriously wounded in the leg he continued to encourage his men and could scarcely be prevailed upon to desist from attempting mounting his horse when so crippled as to be unable to do so.
Other Award: Distinguished Service Cross w/OLC (WWI)

Citation:

The Distinguished Service Cross is presented to Frank C. Bolles, Colonel, U.S. Army, for extraordinary heroism in action near Septsarges, France, September 26, and near Bois-de- Fays, France, September 28, 1918.

On September 26 Colonel Bolles personally directed the assaulting battalion of his regiment when the line was temporarily held up by hostile fire, leading the attacking troops forward to their objective. After reaching the objective, terrific hostile fire caused many casualties, and the line was beginning to waver when Colonel Bolles assisted in the reorganization of the line, and by his personal example of courage and fearlessness encouraged his men to hold in the face of the withering machine-gun and artillery fire until the flank division had advanced abreast. On September 28 he rallied his men under the sweeping fire of machine guns, minenwerfer, and artillery, and although painfully wounded, personally assisted in the reorganization of the positions.
 Other Award: Distinguished Service Cross (Philippine Insurrection)