This study introduces a pretrained large language model-based annotation methodology of the first dependency treebank in Ottoman Turkish. Our experimental results show that, through iteratively i) pseudo-annotating data using a multilingual BERT-based parsing model, ii) manually correcting the pseudo-annotations, and iii) fine-tuning the parsing model with the corrected annotations, we speed up and simplify the challenging dependency annotation process. The resulting treebank, that will be a part of the Universal Dependencies (UD) project, will facilitate automated analysis of Ottoman Turkish documents, unlocking the linguistic richness embedded in this historical heritage.