Currently, there is no comprehensive presentation of trends in oral diseases in the German general population over the last 20 years. How did prevalences of caries, periodontitis, and tooth loss and their determinants change in Germany between 1997 and 2014? We analysed data from 35- to 44-year-olds and 65- to 74-year-olds from the German Oral Health Studies ("Deutsche Mundgesundheitsstudien" DMS) III to V and of 25- to 74-year-olds from the Studies of Health in Pomerania (SHIP‑0 and SHIP-Trend-0). The decayed, missing, filled teeth index (DMFT), the number of sound teeth, the community periodontal index (CPI), and data on tooth count and edentulism were analysed. Regarding determinants, an increase in subjects with high school education, a slight decrease in smokers, and an increase in better oral hygiene patterns was observed in both studies. In 35- to 44-year-olds, the number of sound teeth increased from 11.9 in DMS III to 16.8 in DMS V, while in 65- to 74-year-olds the number of sound teeth increased by 5.9. A similar trend was observed in SHIP. In DMS, the prevalence of the highest CPI score of 4 decreased from 9.3% to 3.5% in 35- to 44-year-olds; in 65- to 74-year-olds, the 2014 prevalence was at the same level as in 1997 (10.5% and 9.8%). In parallel, the percentage of edentulous 65- to 74-year-olds halved in both studies. The number of teeth increased across all age strata. DMS and SHIP consistently showed an increase in the number of healthy teeth free of fillings, a slight reduction of subjects with a CPI score of 4, more tooth retention, and less edentulism. Because of more tooth retention and current demographic changes, higher periodontal treatment needs might be expected for the future.