Deep learning models produce impressive results in any natural language processing applications when given a better learning strategy and trained with large labeled datasets. However, the annotation of massive training data is far too expensive, especially in the legal domain, due to the need for trained legal professionals. Data augmentation solves the problem of learning without labeled big data. In this paper, we employ pre-trained language models and prompt engineering to generate large-scale pseudo-labeled data for the legal overruling task using 100 data samples. We train small recurrent and convolutional deep-learning models using this data and fine-tune a few other transformer models. We then evaluate the effectiveness of the models, both with and without data augmentation, using the benchmark dataset and analyze the results. We also test the performance of these models with the state-of-the-art GPT-3 model under few-shot setting. Our experimental findings demonstrate that data augmentation results in better model performance in the legal overruling task than models trained without augmentation. Furthermore, our best-performing deep learning model trained on augmented data outperforms the few-shot GPT-3 by 18% in the F1-score. Additionally, our results highlight that the small neural networks trained with augmented data achieve outcomes comparable to those of other large language models.