Within Rogers’ person-centered theory, unconditional positive regard (UPR) is considered a key construct for cultivating optimal development and psychological functioning, while its opposite constructs—conditional regard, unconditional negative regard, and unconditional positive disregard—are suggested to undermine these processes. Through a basic interpretive qualitative study, we aimed to explore retired elite figure skaters’ perceptions of and experiences with UPR and its opposites in their relationships with former coaches. In this article, we address participants’ experiences of the opposites of UPR (conditional regard, unconditional negative regard, and unconditional positive disregard) from their former coaches. Qualitative content analysis procedures resulted in five dimensions relative to these constructs: (1) Conditional Regard, (2) Unconditional Negative Regard, (3) Unconditional Positive Disregard, (4) Perceived Influence of the Opposites of UPR, and (5) Power and Coach Regard. Results point to participant reports of learning to regard themselves in the same way their coaches regarded them—positively, negatively, or not at all, with or without conditions. Experiences of the opposites of UPR in coach-athlete relationships were, in turn, reported to undermine participants’ trust in their coaches, detrimentally impact their motivation and performance in figure skating, and influence their development of conditional self-regard, negative self-regard or self-disregard. Lay Summary: In this article, we discuss retired elite figure skaters’ experiences with the opposites of UPR—conditional regard, unconditional negative regard, and unconditional positive disregard—in their relationships with former coaches. Participants’ reported that these experiences had detrimental effects on trust for their coaches, motivation, performance, and self-regard.