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It is a common belief that training deep transformers from scratch requires large datasets. Consequently, for small datasets, people usually use shallow and simple additional layers on top of pre-trained models during fine-tuning. This work shows that this does not always need to be the case: with proper initialization and optimization, the benefits of very deep transformers can carry over to challenging tasks with small datasets, including Text-to-SQL semantic parsing and logical reading comprehension. In particular, we successfully train $48$ layers of transformers, comprising $24$ fine-tuned layers from pre-trained RoBERTa and $24$ relation-aware layers trained from scratch. With fewer training steps and no task-specific pre-training, we obtain the state-of-the-art performance on the challenging cross-domain Text-to-SQL parsing benchmark Spider. We achieve this by deriving a novel Data-dependent Transformer Fixed-update initialization scheme (DT-Fixup), inspired by the prior T-Fixup work. Further error analysis shows that increasing depth can help improve generalization on small datasets for hard cases that require reasoning and structural understanding.