One way, though manual and tedious, would be to shut off all outlets except the one and record the amps. Over time, this might indicate a trend.
I would really be surprised if it would be possible to directly measure amperage individually. This would require seperate circuitry for each outlet. If it were already there, seems the functionality would already exist.
Now, for some real conjecture.

It might be possible to determine amperage for each outlet through analysis by comparing total amperage over time with a log of outlet state. But, it would probably not be accurate enough to be usable.
Todd