This study examined the pedestrians’ safe and unsafe behaviour before and during street crossing in three cities in South Western Nigeria. 1,214 pedestrians were observed at crossing sites using direct observation approach. The data were analysed using descriptive statistics, chi-square, Analysis of Variance (ANOVA) and logistic regression. In all, 730 (60.1%) of the observed pedestrians were male, and 484 (39.9%) were female. The analysis of the data showed that safe crossing practices were generally high, as over 50% of pedestrians at different stages of the crossing process were categorized as exhibiting safe observation behaviour. In terms of crossing tempo, Chi-square test revealed significant difference between male (65.1%) than female (56.0%) pedestrians (χ2=10.12, d=1, p=0.000). While ANOVA showed significant variation in the risky crossing behaviour among the cities (F (2, 1211) =71.93, P< 0.01). Logistic regression analysis showed that adult pedestrians are 0.79 times more likely to exhibit safe crossing behaviour than younger pedestrians and pedestrians are 0.42 times more likely to exhibit safe crossing when vehicles are moving on one side of the road than when there is no vehicular movement. The study suggests measures to enhance safe street crossing behaviour in the sampled cities and other cities in Nigeria.