According to a blog post on Zap2It the total cost to New York for the destruction that fight caused would be roughly 129,000 dead, 250,000 missing, 1,000,000 injured, and a long-term financial cost of $1,000,000,000,000 (one trillion dollars). For comparison, according to the same article, the long term cost of 9/11 was about $55,000,000,000, and the damage for the fight in The Avengers would be about $160,000,000,000.

So, yah, Tony wins.

I Think Iron man just owned superman