This research addresses Natural Language Processing (NLP) tokenization challenges for transitional Chinese, which lacks adequate digital resources. The project used a collection of articles from the Shenbao, a newspaper from this period, as their study base. They designed models tailored to transitional Chinese, with goals like historical information extraction, large-scale textual analysis, and creating new datasets for computational linguists. The team manually tokenized historical articles to understand the language’s linguistic patterns, syntactic structures, and lexical variations. They developed a custom model tailored to their dataset after evaluating various word segmentation tools. They also studied the impact of using pre-trained language models on historical data. The results showed that using language models aligned with the source languages resulted in superior performance. They assert that transitional Chinese they are processing is more related to ancient Chinese than contemporary Chinese, necessitating the training of language models specifically on their data. The study’s outcome is a model that achieves a performance of over 83% and an F-score that is 35% higher than using existing tokenization tools, signifying a substantial improvement. The availability of this new annotated dataset paves the way for refining the model’s performance in processing this type of data.