Recent studies reported that the sex difference in performance in ultra-endurance sports such as swimming and cycling changed over the years. However, the aspect of drafting in draft-legal ultraendurance races has not yet been investigated. This study investigates the sex difference in ultraswimming and ultra-cycling draft-legal races where drafting - swimming or cycling behind other participants to save energy and have more power at the end of the race to overtake them - is allowed. The change in performance of the annual best and the annual three best in an ultra-endurance swimming race (16-km 'Faros Swim Marathon') over 38 years and in a 24-h ultra-cycling race ('World Cycling Race') over 13 years were compared and analysed with respect to sex difference. Furthermore, performances of the fastest female and male finishers ever were compared. In the swimming event, the sex difference of the annual best male and female decreased non-significantly (P = 0.262) from 5.3% (1976) to 1.0% (2013). The sex gap of speed in the annual three fastest swimmers decreased significantly (P = 0.043) from 5.9 ± 1.6% (1979) to 4.7 ± 3.1% (2013). In the cycling event, the difference in cycling speed between the annual best male and female decreased significantly (P = 0.026) from 33.31% (1999) to 10.89% (2011). The sex gap of speed in the annual three fastest decreased significantly (P = 0.001) from 32.9 ± 0.6% (1999) to 16.4 ± 5.9% (2011). The fastest male swimmer ever (swimming speed 5.3 km/h, race time: 03:01:55 h:min:s) was 1.5% faster than the fastest female swimmer (swimming speed 5.2 km/h, race time: 03:04:09 h:min:s). The three fastest male swimmers ever (mean 5.27 ± 0.13 km/h) were 4.4% faster than the three fastest female swimmers (mean 5.05 ± 0.20 km/h) (P ＜ 0.05). In the cycling event, the best male ever (cycling speed 45.8 km/h) was 26.4% faster than the best female (cycling speed 36.1 km/h). The three fastest male cyclists ever (45.9 km/h) (mean 45.85 ± 0.05 km/h) were 32.1% faster (P ＜ 0.05) than the three fastest female cyclists ever (34.7 km/h) (mean 34.70 ± 1.87 km/h). In summary, in draft-legal ultra-distance events such as swimming and cycling, the sex difference in the annual top and annual top three swimmers and cyclists decreased (i.e. non-linearly in swimmers and linearly in cyclists) over the years. The sex difference of the fastest athletes ever was smaller in swimming (1.5%) than in cycling (26.4%). This finding is different to reports from races where drafting was not possible or even prohibited and where the sex difference remained stable over years.