Maize (Zea mays L.) grain yield is severely constrained by drought and this study was conducted to assess gains in grain yield and other traits of released maize cultivars. Twenty-three maize cultivars plus a check were evaluated under drought and well-watered conditions at Zaria and Kadawa during 2015/2016 and 2016/2017 dry seasons. The 24 cultivars were evaluated using 6 x 4 lattice design with three replications. Genotypes differed significantly for all measured traits except anthesis-silking interval (ASI), husk cover, and number of ears per plant under drought, and ASI, husk cover, and ear aspect under well-watered conditions. Under drought, grain yield ranged from 2251 kg ha−1 for SAMMAZ 31 to 4938 kg ha−1 for SAMMAZ 19, with a genetic gain of 1.93% yr−1. Under well-watered conditions, grain yield varied from 3082 kg ha−1 for SAMMAZ 37 to 5689 kg ha−1 for SAMMAZ 51, with the same genetic gain found under drought conditions. Grain yield reduction as a result of drought was 28.4% and performance under drought predicted performance under well-watered conditions better than vice versa with regression coefficient value of 0.8. Grain yield had significant correlations with all measured traits under both water conditions, except for husk cover, plant and ear heights under drought. Our data revealed that substantial genetic gains have been made in breeding for high grain yield cultivars under drought and well-watered conditions over a period of 16 years in Nigeria.