This research study presents comprehensive case studies within the context of school mathematics, focusing on pedagogical practices, assessment strategies, and outcomes associated with the integration of Work-Integrated Learning (WIL). WIL is an innovative educational approach, which aims at bridging the gap between theoretical mathematical concepts and practical, real-world applications (Freudenberg et al. in J Bus Educ Sch Teach 4(1):42–61 (2010) [1]; Govender and Wait in S Afr 31(5):49–64 (2017) [2]). The study investigates how WIL has been implemented by the investigators in distinctive educational setting experientially. This research adopts a qualitative approach, incorporating surveys, interviews, and classroom observations to gather data. Drawing from in-depth observations, interviews, and analysis of assessment data, these case studies reveal the intricate dynamics of WIL in school mathematics. It demonstrates that WIL promotes a deeper understanding of mathematical concepts by allowing students to apply their knowledge in real-world situations. The collaborative engagement of mathematics educators and students in co-creating vocation-building curriculum and delivery enhances students’ mathematical proficiency and cultivates skills crucial for their future careers. Assessment aspects in WIL for mathematics education are complex yet rewarding. The paper outlines various assessment strategies used in this setting, all of which emphasize gauging students’ problem-solving abilities, critical thinking skills, and their capacity to adapt mathematical knowledge to real-world scenarios. The analysis demonstrates that WIL initiatives in mathematics education significantly enhance students’ mathematical proficiency and understanding. These experiences go beyond traditional classroom learning, engaging learners in authentic, industry-relevant projects and problem-solving scenarios. These case studies also identify challenges in implementing WIL, such as the need for professional development for educators, and the importance of maintaining a balance between academic rigor and practical application. In conclusion, these case studies underscore the transformative potential of work-integrated learning to revitalize mathematics education at the school level by fostering deeper comprehension of mathematical concepts and promoting the development of essential skills. By aligning classroom instruction with real-world practice, students acquire the skills, knowledge, motivation, and engagement required for improving mathematical proficiency and its applications. The findings presented here serve as valuable insights for educators, policymakers, and stakeholders seeking to enhance mathematics education through innovative pedagogical practices and assessments that connect theory with practical applications making way towards career readiness. WIL can contribute to the development of mathematically proficient graduates who are well-equipped to make meaningful contributions to various sectors of the economy.