The aims of this study were 3-fold: (1) to compare technical proficiency scores between training and matches for tackling, ball-carrying, and rucking outcomes; (2) to determine the relationship between technique in training and technique in matches for tackling, ball carrying, and rucking; and (3) to determine how contact technique (in training and matches) relates to match performance and injury outcomes. Twenty-four male players from an amateur rugby union club participated in the study. At the beginning of the season, players’ contact technique proficiency was assessed in a training drill. Contact technique in matches was assessed during 14 competitive matches. The technique proficiency was assessed using standardized criteria, and the outcomes of each tackle, ball carry, and ruck were recorded. In training and matches, positive performance outcomes were associated with higher contact technique proficiency scores. For instance, in both settings, tackle technique was significantly lower in missed tackles when compared to effective and ineffective tackles. Players’ contact technique scores in matches also had a positive effect on their tackle performance in matches. Ball-carry technique was associated with tackle breaks in matches (P < .05, r2 = .31). In training and match environments, tackler, ball-carrier, and ruck technique scores were significantly associated with effective tackles, ball carries, and rucks. Despite the relationship between technical proficiency scores and performance, there were small to moderately higher scores in training compared with matches. The current study highlights the importance of contact skill training, in different environments and conditions, to ensure that skills developed in training are transferred to match performance.