The literature recognizes six measures of retention in care, an integral component of the HIV Continuum of Care. Given prior research showing that different retention measures are differentially associated with HIV health outcomes (e.g., CD4 count and viral suppression), we hypothesized that different groups of people living with HIV (PLWH) would also have differential retention outcomes based on the retention measure applied. We conducted a cross-sectional analysis of multisite patient-level medical record data (n = 10,053) from six academically-affiliated HIV clinics using six different measures of retention. Principal component analysis indicated two distinct retention constructs: kept-visit-measures and missed-visit measures. Although black (compared to white) PLWH had significantly poorer retention on the three missed-visit measures, race was not significantly associated with any of the three kept-visit measures. Males performed significantly worse than females on all kept-visit measures, but sex differences were not observed for any missed-visit retention measures. IDU risk transmission group and younger age were associated with poorer retention on both missed- and kept-visit retention measures. Missed- and kept-visit measures may capture different aspects of retention, as indicated in the observed differential associations among race, sex, age, and risk transmission group. Multiple measures are needed to effectively assess retention across patient subgroups.