This has pointed out here before, though I can't find the thread. Wilson also had a higher % of the popular vote his second time around, so I think you have to go all the way back to Andrew Jackson or so to find the last time an incumbent president won a second term with a smaller %age of the popular vote than the first time.
EDIT: And if you want the last time an incumbent president won a second term with both a reduced popular *and* electoral vote %age, I think you have to go back to James Madison....though I don't think every state had a popular vote tally back then.
Oh, you're right. I should have clarified. Wilson did win a larger percentage of the popular vote in 1916, but a smaller share of the electoral vote. Wilson basically dominated the map in 1912 due to Taft and Roosevelt splitting the Republican vote.
I guess that makes the trend even stronger. So if Obama does win with less than 53% of the vote, he'll break a 200 year streak.