Large language models (LLMs) are challenging to deploy for domain-specific tasks due to their massive scale. While distilling a fine-tuned LLM into a smaller student model is a promising alternative, the capacity gap between teacher and student often leads to suboptimal performance. This raises a key question: when and how can a student model match or even surpass its teacher on domain-specific tasks? In this work, we propose a novel theoretical insight: a student can outperform its teacher if its advantage on a Student-Favored Subdomain (SFS) outweighs its deficit on the Teacher-Favored Subdomain (TFS). Guided by this insight, we propose Scheduled Checkpoint Distillation (SCD), which reduces the TFS deficit by emulating the teacher's convergence process during supervised fine-tuning (SFT) on the domain task, and a sample-wise Adaptive Weighting (AW) mechanism to preserve student strengths on SFS. Experiments across diverse domain tasks--including QA, NER, and text classification in multiple languages--show that our method consistently outperforms existing distillation approaches, allowing the student model to match or even exceed the performance of its fine-tuned teacher.