In this case study, we report the experiences and reflections of a female trainee sport and exercise psychologist who navigated the dismissal of a management team and COVID-19 in a professional football club. The trainee delivered an educational intervention to a group of 10 players transitioning from a youth academy to the first team at a professional football club. This formed part of a larger organizational intervention to integrate sport psychology into the club. During the delivery, her mode of working changed from face to face to online support (because of the COVID-19 pandemic), and the management team, except the first author, were dismissed from their duties after lockdown. We discuss the challenges of integrating and working within an organization, experiencing the dismissal of the management team, the effect of the practitioner’s gender as a female working in a male-dominated sport, and the unrelenting football culture and how we, as practitioners, may choose to navigate it. We supplement personal reflections and notes from client work with learning logs and supervision as part of coursework components of a doctorate in sport and exercise psychology. This case study contributes to the literature by presenting and reflecting on challenges that novice practitioners might face working within a professional football organization.