This study investigated the ways in which second-career mathematics teachers exhibit and discuss their knowledge of mathematical connections. Results indicated that the second-career teachers were most likely to exhibit knowledge of mathematical connections when creating a mathematics problem from a given topic and when making a mathematical connection to a context outside of mathematics. The data analysis indicated that those second-career teachers that exhibited knowledge of mathematical connections were hesitant to use this knowledge in their teaching for reasons including their own perception of students’ ability. The implications of these findings inform future preparation and recruitment of second-career mathematics teachers.