The study examines trends in bicycling fatalities reported to the Australian police between 1991 and 2013. Trends were estimated using Poisson regression modelling. Overall, cycling fatalities decreased by 1.9% annually between 1991 and 2013. However, while deaths following multivehicle crashes decreased at a rate of 2.9% per annum (95% CI −4.0% to −1.8%), deaths from single vehicle crashes increased by 5.8% per annum (95% CI 4.1% to 7.5%). Over the study period, the average age of cyclists who died in single vehicle crashes (45.3 years, 95% CI 41.5 to 49.1) was significantly higher than cyclists who died in multivehicle crashes (36.2 years, 95% CI 34.7 to 37.7). The average age of deceased cyclists increased significantly for both types of crashes. The observed increase in single vehicle crashes need to be closely monitored in Australia and internationally. In-depth studies are needed to investigate the circumstances of fatal single bicycle crashes in order to develop appropriate countermeasures.