In October 1903, Drake sailed to Jolo, Sulu, in the Philippines. Serving on the Second and Third Sulu Expeditions, he earned a Silver Star on both of them. While in the Philippines, Drake was recommended for a brevet promotion to Major. He was later awarded the Distinguished Service Cross for his heroism at the siege and taking of Cotta Pang Pang on February 14, 1904. After returning to the U.S., he served at the Boise Barracks, and from August 1906 to January 1909, he did recruiting duty at Fort Slocum. Arriving back in the Philippines, Drake served as a quartermaster at Fort Stotsenburg until March 1912. After he and his regiment returned to the U.S., he served in several positions, including participating in the Pancho Villa Expedition, in which he commanded a motor supply train.