This review assesses the development of oral health habits and status in European adults (35–44 years old) and senior citizens (65–74 years old) over the period of 1996–2016. There seem to be good opportunities for improving oral health habits by brushing twice daily with fluoride toothpaste among adults, as only 33–85% reported doing so. Caries experience was extensive among adults (≥92%). In adults of 23 countries, the mean DMFT score ranged from 6.6 to 17.6 (median 12.1). In senior citizens of 21 countries, the mean DMFT score varied from 14.7 to 25.5 (median 22.0). Repeated cross-sectional studies on caries trends in adults revealed a reduction of the DMFT value by 20%, referring to country-wide data. Among senior citizens, the corresponding reduction was 13%, with a shift in the DMFT components, i.e., with lower MT and higher FT scores. Edentulousness in the age group of 35- to 44-year-olds started disappearing in Europe from the year 2000, and had been markedly reduced in some countries during the last decade. However, the eradication of edentulousness among 65- to 74-year-olds has not yet been reported. Further epidemiological surveys should apply caries diagnostic criteria that, besides representing our contemporary understanding of oral health care, allow comparisons with previous surveys using the WHO criteria. In conclusion, in the last two decades, a decline in caries was observed among European adults, and to a lesser extent among senior citizens. It is expected that the decline in caries will contribute to better oral health of individuals.