Adults aged 55 and older are least likely to play sport. Despite research suggesting this population experiences physical and psychological benefits when doing so, limited research focuses on older adult sport initiation, especially in “adapted sports” such as walking football. The aim of this study was to explore initiation experiences of walking football players between 55 and 75 years old. Semistructured interviews took place with 17 older adults playing walking football for 6 months minimum (Mage = 64). Inductive analysis revealed six higher order themes representing preinitiation influences. Eight further higher order themes were found, relating to positive and negative experiences during initiation. Fundamental influences preinitiation included previous sporting experiences and values and perceptions. Emergent positive experiences during initiation included mental development and social connections. Findings highlight important individual and social influences when initiating walking football, which should be considered when encouraging 55- to 75-year-old adults to play adapted sport. Policy and practice recommendations are discussed.