 However, his ship was shipwrecked at the Portuguese islands of Madeira forcing Gillespie to come ashore by a small boat and he then contracted yellow fever in his first night on the island.After recovery, he rejoined his regiment and fought against the forces of the French Republic in the Caribbean at Tiburon Peninsula, Port-au-Prince, Fort Bizotten and Fort de l'Hôpital.Being made Adjutant-General of St. Domingo, he was at home alone when eight men broke into his house to burgle it.