Traditional classroom furniture dictates that children predominantly sit during class time. This study evaluated the impact of providing standing desks within a deprived UK primary school setting over 8 months using mixed-method approaches. All children within a Year 5 class (9–10-year-olds, n = 30) received an adjustable sit–stand desk, while another Year 5 class (n = 30) in a nearby school retained traditional furniture as a control classroom. At baseline, 4 months, and 8 months, activPAL monitors (PAL Technologies, Glasgow, UK) were worn for 7 days to provide time spent sitting and standing. Behavior-related mental health, musculoskeletal discomfort surveys, and a cognitive function test battery were also completed at all three timepoints. Intervention experiences from pupils and the teacher were captured using focus groups, interviews, and classroom observations. At both 4 months and 8 months, multi-level models revealed a reduction in class time sitting in the intervention group compared to the control group ((β (95%CI) 4 months −25.3% (−32.3, −18.4); 8 months −19.9% (−27.05, −12.9)). Qualitative data revealed challenges to teaching practicalities and a gradual decline in behavior-related mental health was observed (intervention vs. control: 4 months +5.31 (+2.55, +8.08); 8 months +7.92 (+5.18, +10.66)). Larger trials within similar high-priority settings are required to determine the feasibility and cost-effectiveness of providing standing desks to every child in the classroom.