Small schools often serve an important function in the local community, where their staff can enjoy close relationships with pupils, colleagues, and local community members. As with any leadership role, leaders of small schools can face challenges, some of which are unique to the small school context. To better understand these challenges and identify potential solutions to these challenges, a systematic review of the literature was conducted on the challenges and the potential solutions reported by leaders of small schools in the UK. Seventeen studies published between 2000 and 2023 were included for synthesis, which captured the experiences of headteachers of small primary schools in England, Scotland, and Northern Ireland. From meta-aggregating the extracted findings, five challenges were identified: (a) nature of the leadership role; (b) finances and resources; (c) relationship and partnership management; (d) teaching and learning; and (e) schools’ location and accessibility. Five potential solutions to these challenges were noted: (a) inclusive and focused leadership; (b) enhanced finances and pooled resources; (c) developing relationships and partnerships; (d) providing leaders and staff with effective support and Continuing Professional Development (CPD); and (e) enhanced school provision. Suggestions for policy and practice that can help leaders of small schools are discussed.