question: We propose a method for learning entity orders, for example, safety, popularity, and livability orders of countries. We train linear functions by using samples of ordered entities as training data, and attributes of entities as features. An example of such functions is f(Entity) [Formula: see text] (Police budget) [Formula: see text] (Crime rate), for ordering countries in terms of safety. As the size of training data is typically small in this task, we propose a machine learning method referred to as context-guided learning (CGL) to overcome the over-fitting problem. Exploiting a large amount of contexts regarding relations between the labeling criteria (e.g. safety) and attributes, CGL guides learning in the correct direction by estimating a roughly appropriate weight for each attribute by the contexts. This idea was implemented by a regularization approach similar to support vector machines. Experiments were conducted with 158 kinds of orders in three datasets. The experimental results showed high effectiveness of the contextual guidance over existing ranking methods.