Abstract: As self-regulation is crucial in top-level performance, prior investigations aimed at studying the efficacy of the self-regulatory strategy of implementation intentions (i. e., if–then plans) in athletic performance. We investigated the inner obstacles (if) that athletes face in competitive situations and assessed the corresponding goal-directed behaviors (then) to design effective implementation intention theory-based interventions. We asked elite and youth-level cyclists (Study 1; N = 34; age: M = 23.7 ± 9.9 years) with a self-designed questionnaire and used a reworded version for assessing these research questions from a coach’s perspective (Study 2; N = 42; age: M = 50.2 ± 9.8 years). Dealing with demanding situations, pressure, and concentration were the most frequently named inner obstacles, while goal-directed behaviors were preparation, self-encouragement, relaxation (athletes), and concentration (coaches). The results highlight the emotional–psychological challenges that elite and youth-level cycling athletes face and provide insights for sport psychological research with implementation intentions.