This research compared the oral health status of school children in Dili (the capital of Timor Leste) in 2002 and 2014.The 2014 oral health survey of Dili's children replicated the methods of an AusAID-supported oral health survey conducted in 2002. Equal numbers of children were invited to participate from four age groups (6-8, 9-11, 12-14 and 15-17 years). For the 2014 survey, the subdistricts of Dom Aleixo, Cristo Rei, Metinaro and Vera Cruz were randomly selected for inclusion. A questionnaire was used to collect data on demographics and oral health behaviours. Oral epidemiological examinations were conducted by four dentists and five dental nurses.The 2014 survey in Dili recruited 758 participants for the questionnaire and 655 children for the oral examination. In 2014, a lower proportion of children reported brushing their teeth the previous day (97% vs 100%, p=0.01) and a larger proportion reported having toothache (40% vs 19%, p<0.001) (sometimes to very often) during the previous 12 months. The mean number of decayed, missing or filled teeth in the primary plus permanent dentition (dmft + DMFT) was greater in 2014 than in 2002 (4.2 vs 3.5, p=0.01). There was no difference in the prevalence of decay in the primary dentition (39% vs 37%, p=0.61) or the mean number of decayed, missing or filled (dmft) teeth in the primary dentition in 2014 compared to 2002 (2.0 vs 1.8, p=0.47). However, the prevalence of decay in the permanent dentition was greater in 2014 (70% vs 53%, p<0.001) as was the mean DMFT (2.3 vs 1.7, p=0.04). The prevalence of gingival bleeding (65% vs 81%, p<0.001) and calculus (57% vs 86%, p<0.001) was lower in 2014.There was an increase in dental caries experiences in Dili school children between 2002 and 2014, associated with more permanent teeth dental caries experiences.