Context: Ankle sprains are common injuries in sports, but it is unclear whether they are more likely to occur in a specific period of a sporting game. Objective: To systematically review the literature investigating when in a match ankle sprains most likely occurred. Evidence Acquisition: The databases CINAHL, EMBASE, MEDLINE, and SPORTDiscus were searched up to August 2016, with no restriction of date or language. The search targeted studies that presented data on the time of occurrence of ankle sprains during sports matches. Data from included studies were analyzed as a percentage of ankle sprain occurrence by halftime and by quarters. Meta-analyses were run using a random effects model. The quality assessment tool for quantitative studies was used to assess the article’s quality. Evidence Synthesis: The searches identified 1142 studies, and 8 were included in this review. A total of 500 ankle sprains were reported during follow-up time, which ranged from 1 to 15 years, in 5 different sports (soccer, rugby, futsal, American football, and Gaelic football). The meta-analyses, including all 8 studies, showed that the proportion of ankle sprains during the first half (0.44; 95% confidence interval [CI], 0.38–0.50) was smaller than the second half (0.56; 95% CI, 0.50–0.62). For the analyses by quarters, the proportion of ankle sprains in the first quarter (0.14; 95% CI, 0.09–0.19) was considerably smaller than the second (0.28; 95% CI, 0.24–0.32), third (0.25; 95% CI, 0.17–0.34), and fourth (0.29; 95% CI, 0.22–0.36) quarters. Conclusion: The results of this review indicate that ankle sprains are more likely to occur later in the game during the second half or during the latter minutes of the first half.