Ethnic disparities in academic outcomes persist for Latinx youth in the U.S. Therefore, identifying factors that promote academic success in this population is essential. This study examined the interacting effect of components of hope (agency and pathways) and daytime sleepiness on academic outcomes (teacher-reported school engagement, student-reported school support, and GPA from academic records). Participants were 41 low-income, Latinx middle-school students attending a private, Jesuit school. Agency was positively associated with all three outcomes and pathways was positively associated with GPA and school engagement (p < 0.02). Unexpectedly, daytime sleepiness was positively associated with student GPA (p < 0.02). An interaction trend was found between agency and daytime sleepiness in accounting for variance in GPA (p = 0.09). Specifically, the link between agency and student GPA was significant and positive at both high (B = 0.26, p = 0.004) and low (B = 0.52, p = 0.0002) levels of daytime sleepiness, although the magnitude of effects was stronger at lower levels of daytime sleepiness. A trend was also found in the interaction between agency and daytime sleepiness in accounting for student-rated school support (p = 0.08). Post-hoc probing showed that agency was associated with school support at low (B = 0.45, p = 0.01) but not high (B = 0.10, p = 0.41) levels of daytime sleepiness. Given disparities in academic outcomes for Latinx youth, finding ways to promote academic achievement and school connectedness in the middle school years among this population is critical.