The aim of this study was to investigate the effect of prolonged ski racing using skating style on technique choice in a transition section among female and male high-level skiers. Fifty three national-to-elite level skiers (20 females: 26.7 ± 4.8 years, 167.0 ± 6.5 m, 61.0 ± 5.1 kg, and 75.5 ± 68.8 FIS points; 33 males: 25.2 ± 3.5 years, 179.0 ± 5.2 cm, 73.1 ± 5.7 kg, and 73.7 ± 63.2 FIS points) were video recorded along a flat-to-uphill transition section of a course during the 30-km (females) and 50-km (males) races at the 2018 Norwegian National Championships. Across laps, section speeds decreased (
P
< 0.001) in all skiers, with the best-ranked skiers faster than the lowest-ranked (
P
< 0.001), and males faster than females in the first and middle laps. Section speed within each lap was associated with race performance (
r
= 0.76–0.86,
P
< 0.001 in females and
r
= 0.87–0.89,
P
< 0.001 in males). The prevalence of Gear 2 (G2) increased, while Gear 3 (G3) use decreased (both
P
< 0.001) across the subsequent laps, with females preferring G2 more than males in lap one (
P
= 0.027). In long-distance skate-style skiing, transition performance is representative of race performance and skiers decrease the use of the often-faster G3 technique while increasing the use of the slower G2 technique due to prolonged exercise. Especially female skiers should consider adding some flat-to-uphill G3 practice into established training, specifically early in the session before fatigue may occur.