Ordinal regression aims to classify instances into ordinal categories. As with other supervised learning problems, learning an effective deep ordinal model from a small dataset is challenging. This paper proposes a new approach which transforms the ordinal regression problem to binary classification problems and uses triplets with instances from different categories to train deep neural networks such that high-level features describing their ordinal relationship can be extracted automatically. In the testing phase, triplets are formed by a testing instance and other instances with known ranks. A decoder is designed to estimate the rank of the testing instance based on the outputs of the network. Because of the data argumentation by permutation, deep learning can work for ordinal regression even on small datasets. Experimental results on the historical color image benchmark and MSRA image search datasets demonstrate that the proposed algorithm outperforms the traditional deep learning approach and is comparable with other state-of-the-art methods, which are highly based on prior knowledge to design effective features.