Over the years, the educational related problems been faced by orphans during their tertiary education seems to under explored. However, there is a need to investigate this phenomenon in order proffer a precise solution. In respects to the forgoing, this study examined educational challenges encountered by orphaned undergraduates of a public university in Kwara State, Nigeria. Descriptive survey design was adopted for this study with a sample of 258 undergraduate orphans were selected through accidental and snowball techniques. Data were collected with Educational Challenges Questionnaire with reliability coefficient of 0.83. Mean ranking was used to answer the research question while hypotheses were tested with t-test and ANOVA. Results showed that orphaned undergraduates encounter difficulties in getting ICT facilities, financial support, accommodation/hostels, upkeep/welfare, learning resources and many more. Furthermore, the result revealed a significant difference in the educational challenges of male undergraduate orphans and their female counterpart. Also, there was a significant difference in the challenges based on their level with 100 and 500 level undergraduate orphans encountering greater difficulties and respectively. It was therefore recommended that relevant authority should provide basic needs like learning resources, ICT facilities and financial support to support them.