This dissertation is a modified systematic literature review on the topic of difficult countertransferential feelings and racism in the therapeutic dyad. This paper explores and synthesizes the literature relating to the understanding of the psychodynamic processes that underpin the countertransferential feelings in an inter-racial and similar-racial dyad. Clinical vignettes illustrating difficult countertransferential feelings are explored by examining the theories of Freud and Klein, as well as the literature on race and racism of past and contemporary authors. The aim of this dissertation is to offer a psychoanalytic explanation to help understand the underlying psychodynamic processes that are likely to emerge in an inter-racial and similar-racial therapeutic dyad. The themes which emerged from the literature are grouped and presented using clinical vignettes to illustrate the points discussed. Limitations of the study are identified, as are the implications for further research on the topic of difficult countertransferential feelings and racism in the therapeutic dyad.