Recent advances in deep learning led to several algorithms for the accurate diagnosis of pneumonia from chest X-rays. However, these models require large training medical datasets, which are sparse, isolated, and generally private. Furthermore, these models in medical imaging are known to over-fit to a particular data domain source, i.e., these algorithms do not conserve the same accuracy when tested on a dataset from another medical center, mainly due to image distribution discrepancies. In this work, a domain adaptation and classification technique is proposed to overcome the over-fit challenges on a small dataset. This method uses a private-small dataset (target domain), a public-large labeled dataset from another medical center (source domain), and consists of three steps. First, it performs a data selection of the source domain’s most representative images based on similarity constraints through principal component analysis subspaces. Second, the selected samples from the source domain are fit to the target distribution through an image to image translation based on a cycle-generative adversarial network. Finally, the target train dataset and the adapted images from the source dataset are used within a convolutional neural network to explore different settings to adjust the layers and perform the classification of the target test dataset. It is shown that fine-tuning a few specific layers together with the selected-adapted images increases the sorting accuracy while reducing the trainable parameters. The proposed approach achieved a notable increase in the target dataset’s overall classification accuracy, reaching up to 97.78% compared to 90.03% by standard transfer learning.