This study investigated relationship of self-regulation (SR) with retention in Math and Classroom Learning Environment (CLE) through quantitative approach based on survey method. 10th grade students from Public Schools of Punjab were the population of the study. Using random sampling, 997 respondents (Boys = 489, Girls = 508) from two districts (conveniently) were selected. The CLE was explored by using WIHIC scale (Fraser, 2007). Self-Regulation scale (Zimmerman, 2008) measured students’ self-regulation while for retention in mathematics, a scale developed by the researchers was used. For the whole sample, SR, CLE and Retention in Math, were positive and female students had similar perception regarding these variables with respect to their male counterparts. Findings revealed no significant relationship between CLE and SR of students for the whole sample as well; further, no significant relationship between CLE and students’ retention in Math was found but it was significant for females as compared to males. This study should be conducted at large scale and in varied setting for further implications.