Background: The efficacy of condom use in declining HIV transmission may be compromised by their incorrect usage. Much focus has been paid on the regularity of condom usage but consumer mistakes and challenges must be considered. Breakage, slipping, leakage, incomplete use and other problems during the sexual event may compromise the protective role of the condom. Objective: To evaluate through a systematic review of published data, the type, and incidence of error and problems in condom use, and their possible role in reducing the preventive action of condoms. Methods: A systematic literature search for peer-reviewed articles published between January 2000 and January 2019, issued in English in peer-reviewed journals, and reporting the occurrence of condom errors/problems among HIV high-risk populations. Results: Twenty studies representing nine countries met the inclusion criteria. The most predominant mistakes associated with condom use included condom breakage, slippage, delayed condom application, early removal, issues related to erection loss and difficulties with fit and feel were reported, failure to squeeze out air, use of expired condoms, reuse of condom, and wearing the condom outside out were other issues noticed. Conclusions: Condom use problems and mistakes are prevalent across the globe. Educational efforts are needed to empower HIV the at-risk population with confidence and knowledge to improve correct condom use and increase preventive activity