Adolescence is a critical developmental period associated with an increased variety of interrelated risks and vulnerabilities. Previous studies have found associations between early memories of warmth and safeness, as well as emotion regulation, and self-harm and suicidal ideation in adolescence. Additionally, these early emotional memories have been found to be positively linked with some indicators of emotion regulation during this period. The present cross-sectional study extends prior research by exploring the moderating role of emotion regulation in the relationships between early memories of warmth and safeness, as well as each of the following risk-related outcomes in adolescence, in younger (i.e., 13–15) and older (i.e., 16–19) adolescents: suicidal ideation and self-harm and its associated functions (i.e., automatic and social reinforcement. Three self-report measures of these early emotional memories, emotion regulation, and risk-related outcomes, and a sample of 7918 Portuguese adolescents (53.3% females), with ages ranging from 13 to 19 (Mage = 15.5), were used. In both age groups, at high levels of emotion regulation, early memories of warmth and safeness had a greater (negative) effect on suicidal ideation and the automatic reinforcement function of self-harm, compared to at average and low levels of emotion regulation. These findings highlight the enhancing role of emotion regulation on the associations between early memories of warmth and safeness and some risk-related outcomes in adolescents, both younger and older, which reveals the relevance of targeting emotion regulation when preventing or tackling these outcomes, regardless of adolescents’ levels of early memories of warmth and safeness.