There is very little documentary evidence of Gaspar de Guadalupe. He mustered in the company of don Rodrigo Maldonado. Two possible connections exist with other expeditionaries and may shed light on Gaspar's history. Juan de Cepeda was in the same company as Gaspar and he was a native of Toledo. There is a Pasajero record for a Gaspar de Guadalupe from Toledo, suggesting that this Toledo Guadalupe is the expeditionary. Also, expeditionary Rodrigo de Frías received his license for New Spain just five persons after this same Gaspar de Guadalupe. If this reasoning is correct, then his parents were Diego de Guadalupe and María de Guadalupe.
1530-1540:
?AGI, Pasajeros, L.2, E.2582 = Boyd-Bowman, Indice geobiográfico, II:11287 [May 2, 1536, Gaspar, son of Diego de Guadalupe and María de Guadalupe, from Toledo, to New Spain]
1540-1550:
1540, Feb: Muster in Flint & Flint, Documents, Document 12 [1 horse, native arms, in the company of don Rodrigo Maldonado]
?APSM, “Bautismos de Españoles, 1536-1746” [fol.134r: 9 March 1544, Rodrigo, son of Pedro de Zamora and Isabel de Zamora, padrinos were Antón Moreno, Francisco Judiel and his wife, Juan Rodríguez and Ana de Ulloa, wife of Gaspar de Guadalupe]