—Hundreds of studies on Dynamic Geometry Software (DGS) influence on mathematics learning with mixed results have been found in the literature. Correspondingly, this meta-analysis study was conducted to assess the overall impact of DGS and analyze the characteristics of the identified studies to help educators decide under what conditions the use of DGS would achieve a higher level of effectiveness. This meta-analysis study investigated 57 effect sizes drawn from 50 journal articles and international proceedings between 2010 and 2020, using the Comprehensive Meta-Analysis (CMA) program as a calculation tool. Meanwhile, the Hedges coefficient is used to calculate the effect size at the 95% confidence level. Based on a random-effect model with a standard error of 0.09, the analysis found an overall effect size of 1.07. This means that learning using DGS has a relatively high positive effect on math skills. Analysis of the study’s characteristics revealed that the DGS used was more effective by considering sample size, student-computer ratio, and education level. These facts can help educators use DGS in the future. Finally, the study’s implications and limitations are discussed, providing crucial information for further meta-analysis studies on DGS’s impact.