INTRODUCTION: Research on retention in care among men living with HIV (MLHIV) in Sub Saharan Africa is limited. This study examined trends and factors associated with retention in HIV care among men in Wakiso district, Uganda, to identify potential targets for interventions aimed at improving retention. METHODS: We retrospectively analyzed 833 electronic records of MLHIV who were initiated on ART at Wakiso Health Centre IV between January 2018 and December 2021 in two cohorts, MLHIV initiated on ART (January 2018 to December 2019) pre-coronavirus disease 2019 (COVID-19) and (January 2020 to December 2021) during the COVID-19 pandemic. The trends of retention in HIV care were graphically assessed using line plots. A mixed effects modified Poisson model was used to assess factors associated with retention in care. RESULTS: The prevalence of retention in care at 6 months was high (62.9%) pre-COVID-19 and 71.4% during COVID-19 and dropped to below 50% in both cohorts by 24 months. Factors associated with retention in care were ownership of a mobile phone (aPR: 1.10; 95%CI: 1.05-1.28) and (aPR: 1.24; 95%CI: 1.13-1.43). Advanced disease (aPR: 0.76; 95%CI: 0.61-0.94) and (aPR: 0.68; 95%CI: 0.47-0.96) was associated with a lower prevalence of retention. Facility-based groups (aPR: 1.12; 95%CI: 1.02-1.24) were associated with a high prevalence of retention, while facility-based individual management (aPR: 0.91; 95%CI: 0.83-0.99) was associated with a lower prevalence of retention compared to community drug distribution points (CDDP). Multi-month dispensing of over 3-5 months (aPR: 1.51; 95%CI: 1.20-1.90) and 6-months pills (aPR: 1.49; 95%CI: 1.18-1.88) compared to 1-month dispensing was significantly associated with a high prevalence of retention. CONCLUSION: The trend of retention in HIV care among MLHIV in this study declined with increasing duration on ART and may require tailored interventions for men to be retained on lifelong ART. Multi-month dispensing of ART, patients' mobile phones and facility-based groups had a positive influence on retention in care among MLHIV and may be further explored as possible interventions to increase retention in this population.