The COVID-19 pandemic presents challenges to the provision of community programs and access to mental health services for young people. We examined the feasibility, reach, and acceptability of multi-technology delivery of an integrated system that assesses and provides feedback on youth mental health and wellbeing and connects them to care within the context of a youth sports development program. The system was delivered via computer, telephone, and teleconference with 66 adolescent boys participating in a rugby league development program in three communities in Australia. Young people completed online wellbeing and mental health measures (Assess step), parents were provided with telephone feedback on results, support, and referral options (Reflect step), and youth received teleconferenced workshops and online resources (Connect step). The multi-technology delivery was feasible to implement, and reach was high, with barriers experienced at the Assess step but minimally experienced at the Reflect and Connect steps. Delivering the system via multiple forms of technology was rated as highly beneficial and enjoyable by young people. Players improved in self-reported prosocial behaviour, gratitude, and anxiety symptoms from pre- to post-program. Strong collaboration between researchers, organisational personnel, and community members is important for achieving these outcomes.