The horse owner and the multi-disciplinary team (MDT) are responsible for safeguarding horse welfare by ensuring the equipment being used is correctly fitted. The aim of this study was to investigate how saddle fit is assessed, managed, and acted upon by equestrian professionals. Participants (n = 483) completed an online questionnaire, which was split into three major sections: (1) participant demographics; (2) saddle fit for the horse; and (3) saddle fit for the rider. Descriptive statistics, Kruskal-Wallis, and univariable and multivariable analyses were performed (p < 0.05). Inductive content analysis identified themes from open-question responses. From the UK responses (n = 377), 184 saddle fitters, 77 therapists, and 116 coaches completed the survey. Compared to coaches, saddle fitters and therapists asked more frequently when their clients last had their saddle fitted (p = 0.0004). Saddle fitters typically assessed the saddle statically and dynamically vs. therapists, where it was dependent on the circumstances of the assessment (p = 0.0004). Saddle fitters experienced the saddle being out of balance more than therapists (p = 0.032) and made more alterations to the saddle than therapists and coaches (p = 0.0004). This study highlights opportunities for professions within the MDT to better support each other and horseowners to achieve improvements in overall fit for horses and riders.