Digimon season > Pokemon season 1
Darker and more mature (Tai almost killed his sister as a child, Matt and TK's parents are divorced, Izzy's adopted), actual character development, relationships between characters (yeah Ash, Misty, and Brock are friends but there are no real rivalries, tensions, etc) awesome character/monster designs,use of original character's names, arc usage, filler episodes still reveal more about the characters
Pokemon season 1 > all subsequent Digimon seasons (I only watched 2 and 4) and Pokemon seasons (= with 2-5)
Pokemon characters > Digimon characters
Brock and James are the best characters of any children's anime program. Misty is the best heroine of any children's anime program.
Team Rocket's introduction + Pokemon's soundtrack > Digimon (I actually don't remember their soundtrack)
Pokemon wins overall with the exception of season 1 for me when against Digi's season 1