Cycling collisions tend to be less frequent, or at least less frequently reported, than motor vehicle collisions, and as such the safety of cycling infrastructure is more difficult to measure than motor vehicle safety. Nonetheless, there is much that can be learned from an examination of individual cycling collisions. One of the most significant sources of information on the acceptability of cycling infrastructure can be gleaned from examining the outcomes of legal actions involving cycling collisions and falls. The legal system is one way of determining acceptable risk in cycling, and can serve as an important input to cycling infrastructure design, operation, and maintenance. This paper examines the claims, facts, arguments, and outcomes from several legal actions surrounding bicycle collisions and falls in Canada, and determines the lessons to be learned by designers and operators of cycling facilities.