Singapore students have consistently demonstrated outstanding levels of performance in mathematics and problem solving captured in international assessments. However, these stellar results stand in contrast to Singapore's real-world problem-solving capacities, evidenced by her diffident innovation levels and a limited talent pool with problem-solving skills that are high in the value chain. This chapter seeks to address this "skills gap" between what schools develop in students and the high-value workforce skills needed for innovation and enterprise. Focusing on mathematics problem solving, we first examined the historical and socio-cultural development of Singapore mathematics education to identify the system's affordances in cultivating the performance in international assessments, and its trade-offs in developing students' skills in dealing with authentic, non-routine and complex real-world problems. We then examined the trajectories and the impact of pedagogical innovations that were designed for the Singapore mathematics classrooms and that sought to address the trade-offs. From a postulation of factors behind the challenges of implementing and sustaining these innovations in the classrooms, implications for policy, practice, and research are put forth to propose how the Singapore mathematics education can be enhanced to mould the value--creating talent that Singapore needs to stay competitive. [For the complete volume, "Diversifying Schools: Systemic Catalysts for Educational Innovations in Singapore. Education in the Asia-Pacific Region: Issues, Concerns and Prospects. Volume 61," see ED675694.]