Intergenerational play delivers wide-ranging psychosocial and developmental benefits, including strengthened social cohesion, empathy, reduced ageism, and reciprocal learning. However, research has largely prioritised the experiences of children and older adults, often overlooking the perspectives of teachers, parents and funders whose views strongly influence how programmes are understood, supported, and sustained. This paper presents findings from an independent evaluation of a 20-week primary school–based intergenerational play programme delivered between July and November 2025 in Auckland’s Albert Eden Local Board community. The qualitative evaluation draws on stakeholder theory and thematic analysis of ten semi-structured interviews. The teachers and older adults directly involved in the pilot shared closely aligned observations, expectations, and experiences. There was unanimous agreement that feelings of joy and community connection were fostered among the eight children and seven older adults who identified themselves as the ‘Wise and Wonder Crew’. The programme’s capacity to generate secondary relationship-building extending into the playground and wider community was also recognised. Tensions between stakeholder groups nevertheless emerged. Parents, teachers, and older adults believed long term sustainability depended on maintaining intimacy through small, discreet teams where no participant became “lost in a crowd”. The funders, by contrast, emphasised the need for greater reach and spread to justify investment within a constrained funding environment. Consequently, readiness for wider adoption depends on resolving these competing priorities and addressing structural vulnerabilities in the programme’s operational and financial models. A modular delivery model, supported by formalised facilitation and sustainable funding, was recommended to balance relational depth with scale.