BACKGROUND: Much of the driver distraction and inattention work to date has focused on concerns over drivers removing their eyes from the forward roadway to perform non-driving-related tasks, and its demonstrable link to safety consequences when these glances are timed at inopportune moments. This extensive literature has established, through the analyses of glance from naturalistic datasets, a clear relationship between eyes-off-road, lead vehicle closing kinematics, and near-crash/crash involvement. OBJECTIVE: This paper looks at the role of driver expectation in influencing drivers' decisions about when and for how long to remove their eyes from the forward roadway in an analysis that consider the combined role of on- and off-road glances. METHOD: Using glance data collected in the 100-Car Naturalistic Driving Study (NDS), near-crashes were examined separately from crashes to examine how momentary differences in glance allocation over the 25-s prior to a precipitating event can differentiate between these two distinct outcomes. Individual glance metrics of mean single glance duration (MSGD), total glance time (TGT), and glance count for off-road and on-road glance locations were analyzed. Output from the AttenD algorithm (Kircher and Ahlström, 2009) was also analyzed as a hybrid measure; in threading together on- and off-road glances over time, its output produces a pattern of glance behavior meaningful for examining attentional effects. RESULTS: Individual glance metrics calculated at the epoch-level and binned by 10-s units of time across the available epoch lengths revealed that drivers in near-crashes have significantly longer on-road glances, and look less frequently between on- and off- road locations in the moments preceding a precipitating event as compared to crashes. During on-road glances, drivers in near-crashes were found to more frequently sample peripheral regions of the roadway than drivers in crashes. Output from the AttenD algorithm affirmed the cumulative net benefit of longer on-road glances and of improved attention management between on- and off-road locations. CONCLUSION: The finding of longer on-road glances differentiating between safety-critical outcomes in the 100-Car NDS data underscores the importance of attention management in how drivers look both on and off the road. It is in the pattern of glances to and from the forward roadway that drivers obtained critical information necessary to inform their expectation of hazard potential to avoid a crash. APPLICATION: This work may have important implications for attention management in the context of the increasing prevalence of in-vehicle demands as well as of vehicle automation.