Knowledge distillation is a key technique for transferring the capabilities of large language models (LLMs) into smaller, more efficient student models. Existing distillation approaches often overlook two critical factors: the learning order of training data and the capacity mismatch between teacher and student models. This oversight limits distillation performance, as manifested by the counter-intuitive phenomenon where stronger teachers fail to produce better students. In this work, we propose Curriculum Learning-Guided Progressive Distillation (CLPD), a unified framework that explicitly accounts for both factors by aligning data difficulty with teacher strength. CLPD constructs an explicit curriculum by organizing training examples from easy to hard, while simultaneously applying an implicit curriculum over supervision signals by progressively scheduling teachers of increasing capacity. Our framework is modular and can be integrated into standard distillation algorithms with minimal overhead. Empirical results on the reasoning benchmarks demonstrate that CLPD consistently outperforms standard distillation, data ordering alone, and teacher scheduling alone across multiple settings. These findings highlight the importance of jointly considering data ordering and teacher capacity when distilling reasoning abilities into small language models.