Purpose: To describe and compare the race characteristics, demands, and durability profile of a male and a female Grand Tour winner. Methods: Overall and stage-type-specific (ie, time trials, flat, semimountainous, and mountain) demands and race characteristics during 2 Grand Tours were determined and compared between the female and male cyclists. In addition, relative power output distribution and pacing, percentage of functional threshold power (FTP), and changes in maximal mean power outputs (MMPs) with increasing levels of kilojoules burned were determined. Results: Although many differences were found between course and absolute racing demands between the male (FTP: 413 W; critical power: 417 W) and female (FTP: 297 W; critical power: 297 W) cyclists, similar power distributions and pacing strategies were found if data were expressed relatively. However, the female cyclist rode a higher percentage of her FTP during the first 2 quarters of flat stages (14.7%–15.1%) and the last quarter of mountain stages (9.8%) than the male cyclist. Decrements in MMPs were only observed after burning 30 kJ·kg−1 in the female and 45 kJ·kg−1 in the male Grand Tour winner. Conclusions: Both the male and female Grand Tour winners produced very high 20- to 60-minute MMPs, whereas decrements in MMPs were only observed after having burned 75% (female) and 80% (male) of total kilojoules burned during a stage. These are the latest and lowest in MMPs reported in the scientific literature and highlight the importance of durability in combination with excellent climbing and time-trial skills, which are needed to be able to win a Grand Tour.