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This study examined the influence of socioeconomic status, prior achievement, and perceived school connectedness in relation to academic self-efficacy, task interest and self-regulated learning (SRL) behaviors on middle school students’ mathematics achievement. Data about student motivation beliefs and connectedness were obtained from 363 middle school students, while mathematics teachers provided information about students’ SRL skills. Structural equation modeling revealed excellent fit indices for the proposed theoretical model. In addition to the model explaining 54% of the variance in mathematics achievement, key findings involved five unique predictors of mathematics achievement, the importance of school connectedness in predicting student motivation, and the key mediation roles exhibited by self-efficacy and SRL behaviors. Implications for practice are discussed.