Air pollutants, especially PM, have been found to determine various effects on human health, including genotoxic effects. The aim of this study was to assess DNA damage with micronuclei (MN) and comet tests on buccal cells of 6–8 years old children living in an area with high air pollution. Both tests were repeated in the same children in two consecutive winters to compare the levels of DNA damage under different pollution conditions. A complete data set including lifestyle, air pollutants levels and biological sampling was available for 180 children in the two winters. A high mean MN frequency was found in both seasons, with higher value in the first (0.51 ± 0.59) than the second winter (0.40 ± 0.52), whereas DNA damage measured with comet test showed higher damage in the second versus the first winter (visual score 208.8 ± 67.1 vs. 173.2 ± 50.8). The associations between air pollutant levels (CO, NO2, SO2, benzene, O3, PM10, and PM2.5; PM0.5 and PAHs) and DNA damage were investigated at different lag times, and mainly, no significant association was found. This study on repeated measure of MN frequency and DNA damage in children’s buccal did not show an association with various air pollutants evaluated in an area with high levels of air pollution.