The objective of this study was to identify frequency and predictors of gaps in care in a longitudinal cohort of HIV-infected patients in urban New England. We conducted a retrospective cohort study in Providence, RI, of 581 newly diagnosed HIV patients >18 entering into care from 2004 to 2010, and followed their care through the end of 2011. The outcome of interest was gaps in care, defined as an interruption of medical care for >6 months. Time to the first gap was characterized using Kaplan-Meier (KM) curves. Anderson-Gill proportional hazards (AGPH) model was used to identify the risk factors of recurrent gaps in care. During the study period, 368 patients (63%) experienced at least 1 gap in care, 178 (30%) had ≥2 gaps, 84 (14.5%) had ≥3 gaps, and 21 (3.6%) died; 77% of the gaps were followed by a re-linkage with care The KM curves estimate that one-quarter of patients (95% CI = 22-29%) would experience ≥1 gap in care by Year 1; nearly one-half (CI = 45-54%) by Year 2; and 90% (CI = 93-96%) by Year 8. A prior gap was a strong predictor (HR = 2.36; CI = 2.16-2.58) of subsequent gaps; other predictors included age <25 (HR = 1.29; CI = 1.04-1.60), and no prescription of ART in first year of care (HR = 1.23; CI = 1.01-1.50). The results of this study suggest that a significant proportion of newly diagnosed HIV-infected patients will experience multiple gaps in care and yet re-engagement is possible. Interventions should focus on both prevention of gaps as well as re-engaging those lost to follow-up.