Aims: To investigate whether there has been further improvement in the risk of adverse outcomes in pregnancies in women with diabetes during 2008–2016 in Bavaria, Germany. Methods: Using cross-sectional data on all 1716 170 deliveries in Bavarian hospitals between 2001 and 2016, we assessed the risks of stillbirth, early neonatal death, preterm delivery, large for gestational age, malformations, low Apgar score and low umbilical cord pH by maternal group with diabetes (gestational, pre-gestational, or none) separately for 2001–2007 and 2008–2016. We also investigated the associations of specific risk factors such as maternal smoking with respect to early mortality and malformations in each group with diabetes during 2008–2016. Results: No further reduction in the risk for any adverse outcome in mothers with pre-gestational diabetes and their offspring during 2008–2016 was observed. Maternal smoking, multiple delivery and substandard antenatal care were the strongest additional predictors of both early perinatal mortality and malformations for mothers with pre-gestational diabetes. The respective risks were lower and also decreased over time for mothers with gestational diabetes. Conclusions: No significant improvement has been achieved in the management of pregnancies affected by pre-gestational diabetes during the last decade. The apparent risk reductions in women with gestational diabetes may partly be due to a change in diagnostic criteria over time. Women with pre-gestational diabetes who smoke, carry more than one child, or are not regularly seen during pregnancy, may need particular attention.