The study of anticipation in truly expert performers can provide insight into how they cope with extreme time constraints. The purpose of this dual-experiment paper was to investigate individual differences; in anticipation of the penalty corner drag-flick, its trainability, and transfer of improvement to field settings. Australian international and national male field-hockey goalkeepers participated. In experiment 1, international and national goalkeepers (n = 11) completed a penalty corner drag-flick temporal occlusion task that presented; defensive runner positioning at the penalty spot, drag-flicker kinematics, and ball flight. Results indicated seven goalkeepers integrated runner contextual and drag-flicker kinematic information to anticipate above chance. The cause of individual differences was independent pick-up of run and kinematic cues that presented greater opportunity to integrate sources for anticipation. In experiment 2, a sub-sample of goalkeepers participated and received temporal occlusion training or no training. Results indicated individualized improvement in anticipation across video, field, and competition assessments for those that received the intervention, but not controls. Improvements on video test were retained for six months. An individual differences approach can identify deficiencies in anticipation, which can be improved through perceptual training that transfers to motor responses. This contributes to theoretical and practical knowledge to develop anticipation skill.