Background: The risk of developing a state of low energy availability (LEA) (<30 kcals/kg free-fat mass) in endurance athletes is known and recommendations for nutrition are available. However, information on male adolescent cyclists and the influence of hot temperatures is limited. Objectives: The aim of this study was to investigate the impact on energy availability of two 4-day nutritional intervention strategies: (1) supplementary carbohydrate (CHO) intake during exercise and (2) designing and implementing individual nutritional interventions. Methods: Each intervention was preceded by a 4-day basal assessment. Eight competitive male junior road cyclists (aged 16–17 years) were investigated using a 4-day diet and activity records, alongside bioelectric impedance analysis. Their real-time power output, interstitial glucose, and temperature were recorded via sensors and a bike computer. Their energy intake (EI) was estimated from daily, self-reported food diaries. Results: Overall, 100% and 71% of the cyclists were in a state of LEA during the baseline assessment of the supplementary CHO and nutritional interventions, respectively. LEA prevalence, not modified by supplementary CHO intake alone (from 100% to 87%, ns), was markedly reduced by the individual nutritional intervention (from 71% to 14%, p < 0.05). When considering all the data as a whole, LEA was positively influenced by the training load (OR 1.06; 95% Cl 1.03 to 1.09) and free-fat mass (OR 1.46; 1.04 to 2.04) and was negatively affected by EI (OR 0.994; 0.991 to 0.997). A hot environment (air temperature) failed to influence the LEA or glucose dynamics. Conclusions: the nutritional intervention, but not the supplementary CHO intake, markedly reduced the prevalence of LEA in adolescents, who often fail to match their energy expenditure with their energy intake during the competitive season. Nutritional education is essential for adolescent endurance cycling teams.