This study explored the characteristics, contextual factors and consequences of counterfactual thoughts in seven elite athletes using interpretative phenomenological analysis (IPA). Counterfactuals were experienced regularly with self-directed and upward counterfactuals (cognitions about how things could be better) being most frequent. These upward counterfactuals typically occurred following performance that was below participants’ goals and expectations. These thoughts were perceived by participants to have a negative affect initially, and that they then led to facilitative behavioral consequences around learning and development. Some elements of counterfactual thinking could be used as a useful reflective tool to encourage elite athletes to problem solve and motivate cognitive, emotional and behavioral change to enhance future performance.