Looking it up, the Red Wings had 1 more playoff victory in the 1990s than they did in the 2000s (9 playoffs each decade, the 90s missing the playoffs once and the 2000s losing one to a lockout). Based on the overall banner count, 22 to 15 in favor of the 2000s. Top seed in the West five times in the 2000s to three times in the 90s.
It seems like it should be the 2000s. But it doesn’t feel right, because it’s really just 1990 and 1991 dragging the 1990s as a whole down like an anchor. The 1995-1998 teams were basically thisclose to being a dynasty with two Cups and two President’s Trophy losses to New Jersey and Colorado, while the 2000s didn’t exactly put up a sustained threat at being a dynasty. The 1990s had San Jose, but the 2000s had losses to Los Angeles, Anaheim, Calgary, and Edmonton peppered throughout.
Maybe give them bonus points for thriving and not falling apart immediately post-lockout.