Having used an Alesis io2 Express, I am confused by your approach to this; where are you getting your headphone signal?
The io2 has a "monitor mix" function with its own little knob on the top of the interface (just to the left of the main volume output). This allows you to monitor the DAW output (fully clockwise - "USB"), your "dry" input (fully counter-clockwise - "DIRECT") or any blend between the two signals.
Using this feature, if your headphones are plugged into the io2, you will still hear your delayed input in the DAW output IF ECHO IS TURNED ON for that track. IF ECHO IS OFF, you should only hear the dry input blended with the DAW output.
(BTW,
daveny5 - if ASIO
is being used with this interface, it is undoubtedly ASIO4ALL, and I know how you feel about that... me, too, for the record, although I worked with it the entire year I used the io2).