In this thesis, I measure the relationship between the electoral success of municipal incumbents and municipal population size in Canada. I first ask how municipal incumbent success rates vary by municipal population size, and discover that acclamations drive overall population-size based trends of municipal incumbent success in Canada. Using an original dataset and a novel modeling approach that accounts for acclaimed incumbents, I find that municipal incumbent success rates generally fall as municipal population size increases. Furthermore, this relationship is particularly strong in Quebec. After excluding acclamations from the analysis, incumbent success rates increase as population size increases. Thus, voters in large municipalities favour incumbents when compared to their counterparts in smaller municipalities. To further investigate this trend, I then ask how the strength of an incumbency cue changes depending on population size, and find that incumbency cues have a stronger effect in larger municipalities. Taken together, these findings reveal that size-related patterns municipal incumbency in Canada are likely dependent on how voters from different sized municipalities process political information and view incumbent candidates.