Purpose: To improve school organisational performance and innovativeness, and meet diverse student needs, school leaders should be innovative, risk-takers and proactive, thus applying entrepreneurial practices/strategies and market mechanisms. This study aims to investigate, from a schoolteacher's perspective, the degree of entrepreneurial leadership behaviour (ELB) applied by school principals in European primary schools. Given that school autonomy is perceived as an important predictor of leaders' entrepreneurship, this study investigates the impact of educational macro (autonomy and accountability) and micro (demographics) contexts on ELB by comparing centralised and decentralised European school systems with the highly centralised Greek school system. Design/methodology/approach: This comparative study was conducted in Greece (630 participants) and in 14 European countries (972 participants). Thornberry's Entrepreneurial Leadership Questionnaire was used, comprising general entrepreneurial leader (GEL), miner (MIN), accelerator (ACC), explorer (EXP) and integrator (INT) behaviours. Findings: The results revealed that ELB is a multi-dimensional concept, and that all participating teachers perceived ELB application moderately, with more focus on the internal (than external) school environment. Furthermore, the dual-directional macro-contextual influence found in applying ELB indicates that high school autonomy and accountability activate ELB owing to the school's freedom to engage in entrepreneurial ventures, while low autonomy/accountability still activates ELB, but only for organisational survival within hierarchical-bureaucratic school environments. This feature differentiates "intrapreneur/intrepreneur" from "entrepreneur" school principals. Originality/value: The theoretical basis of entrepreneurial leadership (EL) in education should include entrepreneurial multi-dimensional leadership aspects (competencies, behaviours, skills) and educational context (macro and micro). Implications for school leadership research and practice are also discussed.