Warfighters develop and maintain their skills through training. Since fully-manned live training in the real world is often too expensive (by many measures), scientists have developed many types of training systems ranging from classroom sessions to those using virtual reality. Recently, researchers have used augmented reality (AR) to insert virtual entities into the real world, attempting to create a low cost, repeatable, and effective substitute for fully-manned live training. However, very little evaluation of the effectiveness of AR for training has been performed. We performed a pilot study to evaluate the use of wearable AR in teaching urban skills, specifically, room clearing in teams. Eight teams of two were briefed on room clearing techniques, given hands-on instruction, and then allowed to practice those techniques with or without the AR system. After this instructional period, subjects performed several room clearing scenarios against real people using infrared-based practice weapons that logged the number of hits on the subjects and the enemy and neutral forces. During these trials, a subject matter expert evaluated how well the subjects applied the room-clearing techniques. In this paper, we describe the pilot study in more detail, including the hardware and software testbed, and then provide an analysis of the results of the pilot study.