Crossing a two-way street is a complex task that involves visual, cognitive and motor abilities, all of which are known to decline with ageing. In particular, older pedestrians may experience difficulties when crossing two-way streets because of incorrect gap acceptance choices and impossible or unperceived evasive actions. To understand the overrepresentation of older pedestrians in crash statistics, several experimental studies have sought to identify traffic-related factors as well as those related to the abilities of the individuals themselves. However, none of these studies has required participants to actually walk across an experimental two-way street with curbs, which is a particularly challenging situation for older pedestrians. To fill this research gap, a quasi-experiment was conducted in a simulator including a total of 58 healthy aged participants (25 younger-old [age 60–72] and 33 older-old [age 72–92]) and 25 young adults (aged 18–25 years). Participants carried out a street-crossing task in a simulated two-way traffic environment; curbs were present on both sides of the experimental street. Participants also undertook a battery of tests to assess their visual and cognitive abilities. In addition, during the experiment, the participants’ gait parameters were recorded. In line with earlier findings, the older-old group of participants made a higher number of decisions that led to collisions with approaching cars compared with the other groups. The two groups of older participants experienced specific difficulties when vehicles were in the far lane or when they approached rapidly. A regression analysis identified visual acuity, speed of processing (assessed using the UFOV® test), and step length as significant predictors of collisions. Our results have implications for understanding the difficulties experienced by older pedestrians and allow to draw up several recommendations for improving their safety.