Land cover data is an inventory of objects on the Earth’s surface, which is often derived from remotely sensed imagery. Deep Convolutional Neural Network (DCNN) is a competitive method in image semantic segmentation. Some scholars argue that the inadequacy of training set is an obstacle when applying DCNNs in remote sensing image segmentation. While existing land cover data can be converted to large training sets, the size of training data set needs to be carefully considered. In this paper, we used different portions of a high-resolution land cover map to produce different sizes of training sets to train DCNNs (SegNet and U-Net) and then quantitatively evaluated the impact of training set size on the performance of the trained DCNN. We also introduced a new metric, Edge-ratio, to assess the performance of DCNN in maintaining the boundary of land cover objects. Based on the experiments, we document the relationship between the segmentation accuracy and the size of the training set, as well as the nonstationary accuracies among different land cover types. The findings of this paper can be used to effectively tailor the existing land cover data to training sets, and thus accelerate the assessment and employment of deep learning techniques for high-resolution land cover map extraction.