Background: Motor control and skill acquisition research have contributed greatly to understanding the learning process in sport, but very little of this knowledge has been applied in practice over the past fifty years. The characteristics of expertise in the two major cricket skills, batting and bowling, are well established but the training environments used to develop them are yet to be characterised. Recommendations on the how the ball is delivered (feed), decision making, task variability and information sources for skill development in cricket have been made previously in research. To promote skills which transfer between the training and performance environments, tasks should maintain the connection between the person, their task and the environment. Coaches have found it difficult to apply complex learning designs to their practice because the underpinning concepts remain unclear. Demystifying evidence-based practice for skill development in cricket is needed to make research knowledge more accessible for coaches. Purpose: Given club level cricket (amateur) is the stepping-stone of the talent development pathway for junior representative players pursuing elite status, it is important to evaluate the effectiveness of skill development practices at this level and identify means of improvement. Methods: A categorical assessment tool was developed to assess 21 training sessions performed during an amateur women’s cricket team throughout the 2018/19 season. We assessed how the ball was delivered (feed), decision making elements, variability and sources of information available to ascertain the representativeness of each training session according to published research on skill development and expertise. The tool featured a scoring range (0–3) with maximum scores per discipline of 12 for bowling and 15 for batting. Key performance indicators (KPI), outlined by the head coach, were also collected during the season to assess game performance and explore any connections with training design. Results: A lack of variability in training design between the 21 sessions performed (<0.5 units on 0–3 scale) did not allow for a correlational analysis with game performance. In contrast, game KPIs were achieved sporadically throughout the season. The most representative training elements were provided for bowling feed (target), decision making and variability, while batting feed (type) and variability also scored well on the assessment tool. The maximum score for representativeness for bowling or batting was not reached, and training design remained largely unchanged throughout the season despite changes in match type, competition phase and consistent low scores in some elements.Conclusions: Some elements of representative learning design were apparent in this amateur cricket setting but only in discrete areas of training. Despite changes in the competition phase and match type, there was a lack of adaptation in training design. Future research is needed to evaluate the principles of representative training design and their effect on cricket skill development and match performance. A more sensitive categorical assessment tool may also be necessary to detect subtle changes in training design.