The purpose of this study was to conduct a quantitative, exploratory analysis of key variables at transition grade levels (i.e., 7th, 9th, 12th) toward retention and completion in postsecondary education among Gaining Early Awareness and Readiness for Undergraduate Programs (GEAR UP) students. The exploration included variables that were retrieved from existing data on 65 students from one of the state's GEAR UP subawards in order to conduct correlations, t-tests, sign tests, and binomial regression to explore the variables across the transition years in relation to GEAR UP participation and postsecondary outcomes. Students represented by the data were GEAR UP participants since their 7th-grade year, having engaged in twice monthly peer-mentoring and summer programming activities within a university partnership. Importantly, most students were of Latinx heritage backgrounds, and the majority enrolled in postsecondary education; notably, the 4-year postsecondary completion rate was 84%. A discussion and conclusion of this exploratory analysis are provided.