In the end Skyrim wins it for me, although not by much.
Biggest pros for Skyrim are the landscape and the main quest. Oblivion's main quest was simply bad. Skyrim dungeons take a little longer to get repetitive but still they do, too soon.
Cities were better in Oblivion. They felt bigger, more unique and you have the huge Imperial city in the center with lots of things to do including the Arena challenges. The cities in Skyrim have 1 shop of each kind at most and most villages don't even have more then 5 buildings. There are more guards then inhabitants in each stronghold.
I preferred the thief and assassins guild quest lines in Oblivion. Mage quest line is better in Skyrim. Both have there equal share of unique extra quests although the Oblivion quest where you go inside the painting is unmatched. Skyrim wins it in sheer number of quests, although the percentage of go here and get or kill x quests is too high imo.
I spent over 100 hours on each game before getting bored, both are very good. Apart from the graphics and more content in Skyrim I don't really see all that much difference between the 2.
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