Coach leaders/administrators in diverse amateur and grassroots football contexts are increasingly accountable for sustaining strategic, state-of-the-art, evidence-based, effective, and efficient programs, initiatives, and services. However, coach leaders/administrators within these organizational settings face significant challenges (e.g., insufficient organizational support and research expertise) in enacting research-informed and evidence-based practices. Strategic Educational Inquiry (SEI) is a flexible and rigorous approach to practitioner research and is particularly useful for coach leaders/administrators to gather evidence for quality assurance and enhancement purposes. This paper critically examines whether and how SEI is applied in diverse amateur/grassroots football coaching contexts. Drawing on case study research using multiple case design, preliminary findings from this study indicate that SEI situates specific amateur/grassroots coaching programs and initiatives within the relevant research and professional literature; it focuses SEI on organization-specific priority research objectives, ethical inquiry, and appropriately aligned research methodology; and involves systematic data collection, data analysis, and dissemination of best practices. Critical organization-specific supports to facilitate implementation of SEI in diverse amateur/grassroots football contexts include: strategic coach education and skills training (e.g., access to state-of-the-art customized technology-enabled professional development experiences and expert mentoring support).