This chapter discusses teacher education efforts and analyses the research outcomes in the domain of solving problems in real-world contexts, particularly in the field of mathematical modelling among other tasks situated in real-world contexts in Singapore mathematics classrooms. The first part of this chapter begins with an understanding of “applications and modelling” from the perspective of the Singapore school mathematics curriculum framework. The second part of this chapter reports on the efforts made in supporting applications and modelling in teacher education through professional development opportunities. This chapter continues with a discussion of findings from local research in solving problems in real-world contexts (applications and/or modelling) carried out with students in primary and secondary schools to add to the repertoire of knowledge in this domain. Challenges are surfaced in the light of the preceding sections with implications for teacher education and research with the acknowledgement that there is still some distance to go to know more about applications and modelling and actualizing the curriculum in a more holistic sense through teacher education and the implementing of modelling lessons. This chapter discusses the way forward in supporting the advancement of mathematical modelling in the mathematics curriculum.