Master of Arts / Department of History / Marsha L. Frey / The diplomatic corps employed by Oliver Cromwell and Charles II from 1649 to 1660 differed greatly. This study will focus on the top three diplomatic ranks: ambassador, envoys and residents and will exclude agents and chargé d′affaires. The lesser ranks have been excluded for several reasons primarily because biographical information does not exist for many of them and as lesser diplomats their missions were not significant and often lasted only a matter of days. This prosopographical examination of the twenty-four diplomats employed by Charles II and Oliver Cromwell provides insight into their similarities as well as their differences. After examining the twenty-four, one from each side will be further researched. In matters of religion, Cromwell predictably sent Protestants. Charles also sent Protestants, but did send Roman Catholics, especially to Catholic courts. Despite the age difference between Cromwell and Charles II, age did not separate their diplomats. The average age of Cromwell’s and Charles’ II diplomats was both forty years. In matters of education, those who went to college had a tendency to choose the Puritan-influenced Cambridge for the Commonwealth and Protectorate and Oxford for the Royalists. The area a diplomat was from shows that the diplomats from north chose the side of the Commonwealth while those from London and south chose the Royalist side. Royalists had a higher percentage of military service and a higher percentage of Parliamentary service. Although more Commonwealth and Protectorate diplomats had a university education, the Royalists had a higher percentage of master’s degrees and the study of the law. When looking at a diplomat’s position in a family, the Commonwealth diplomats had a greater chance of being the oldest son, while the Royalists tended to be younger sons. This information is valuable because it expands the commonly held historiographical image of the typical Royalist and Commonwealth supporters and illustrates the differences between the general support and each sides diplomatic corps.