The purpose of this pilot study is to investigate the differences of eye movements among three different flight backgrounds. There were eleven participants (2 military pilots with average 2,250 flying hours, 6 commercial pilots with average 5,360 flying hours, and 3 novices). All participants wear a mobile eye tracker during the experiment operating a Boeing 747 flight simulator for landing. The eye tracker recorded all participants’ eye movement data automatically. The average values of the latency of first fixation (LFF) and the total contact time (TCT) for five regions of interest (ROIs) are used to examine proposed hypotheses. The findings include: (1) participants of different flight backgrounds have different sequences of viewing ROIs; (2) participants of military pilots and novices spent most of time viewing the outside of cockpit (ROI-3); however, participants of commercial pilots spent most of time viewing the Primary Flight Display (ROI-1). Current research findings might be applied for developing conversion training for military pilots conversed to civil airlines pilots. The fundamental reasons of why pilots viewing ROIs in different sequence and spending significant different time on the ROIs needed to be studied further in the future.