Previous research has investigated the representational translation practices of high school students, high school teachers, and college preservice teachers in various mathematical contexts including linear functions. Findings from qualitative research has frequently led to new notions about participant work and understanding. Many quantitative research has investigated the degree to which some in these populations correctly perform these translations. However, it seems that only infrequently have empirical research investigated findings from qualitative studies and vice versa, and findings regarding one population are rarely compared with findings of another population. This study (a) empirically explores the frequency of success of preservice teachers (N = 80) regarding representational translations in the context of linear functions, (b) quantifies results from previous qualitative, literature-based research regarding high school students and teachers, and (c) quantitatively compares the results. This study demonstrates that some mathematical representational translations are more difficult than others.