With an increasing number of parents engaged working on shift and the severity of grade retention in Macao, the present study aims to investigate how parental work schedule influences parents’ involvement in students’ education, student’s self-regulated learning in Mathematics as well as student’s experience of grade retention in Macao. Moreover, few studies have attempted to investigate the relationship among parental involvement, a student’s SRL and student’s experience of grade retention. Therefore, the aim of this paper is to understand the relationship among them. 610 eighth grade and eleventh grade students participated in present study. The quantitative analyses of questionnaires were conducted. Results evinced that (a) mothers engaged working on shift provide less help in homework and set less TV rules to their children, (b) fathers engaged working on shift had more communication and school involvement but with lower educational expectation to their children, (c) families with both parents engaged in shift work had significantly higher scores in parent-child communication and fathers’ involvement in school than those that have fathers engaged in shift work but mothers did not engage working on shift, (d) students had experience of grade retention reported lower father-child communication, parental school iii involvement, parental educational expectations, less Web rules, fathers’ homework help, and had lower level of self-regulated learning competence in Mathematics. The limitation and implication of this study are also discussed.