Rubuta ci gaba ga wannan sakin layi - A ranar 14 ga Yuni, 1898, Paddock da Rundunar Sojoji ta 6 sun bar Florida zuwa Cuba da kuma Spanish-American War. A can ne aka san shi don ƙarfin hali a lokacin yakin San Juan Hill
a cikin Santiago Campaign. Duk da yake a Cuba, Paddock ya kamu da zazzabin cizon sauro, kuma ya kasance a kan rashin lafiya a watan Satumba na shekara ta 1898. Duk da ganewar asali mai kyau, Paddock yana kan izinin likita sau da yawa ko a karkashin kulawar likita a cikin 1899 yayin da yake zaune a Fort Leavenworth.