The herbicide glyphosate (N-phosphonomethylglycine) has been the most commonly applied herbicide worldwide for the past 40 years. This review aims to present and discuss the state of knowledge concerning groundwater contamination by glyphosate and its metabolite, aminomethylphosphonic acid (AMPA). A dataset of 48 reports and articles reporting glyphosate and AMPA detection in groundwater worldwide was constructed from published literature. Specific attention was given to the analysis of available studies on glyphosate and AMPA transport in groundwater to investigate groundwater contamination factors. The information presented in this review highlights detectable groundwater contamination in several countries globally, with many cases exceeding European groundwater quality standards. Both agricultural and non-agricultural applications of glyphosate can be significant sources of pollution, and proximity to agricultural fields is a significant risk factor. AMPA has two primary sources, glyphosate and amino polyphosphates, but very little information is available about the origin of AMPA detected in groundwater. Glyphosate and AMPA transport to groundwater can be significant in well-structured soils rich in macropores, where it generally occurs via preferential flow. An inverse relationship was highlighted between the groundwater depth and glyphosate and AMPA occurrence and concentration in groundwater; however, some discrepancies among the studies were identified. Heavy rainfall shortly after glyphosate application poses a high risk of its transport to groundwater. Seasonal trends in glyphosate and AMPA in groundwater, related to application timing, agronomic practices, and weather conditions, were also observed. Finally, risk-management measures are proposed.