Delay at multiple outputs

I wonder if is possible to delay more than one mono/main output separately, that is if I am placing extra speakers at 50 ft and 100 ft from the FOH, is there a way to delay the two sets of extra speakers at different delay settings (i.e. 50 ft and 100ft)? I tried to put more than one mono mix output on the desktop, but they are all the same output.
Perhaps I have to delay the first set (50ft) on the mono output and the 2nd set of speakers on a post fader aux? Yes?

Yep. The line delay is applied to the bus, as opposed to the physical socket. Your situation would be an ideal use for a matrix. Set it up post fader, feed it with LR and dial in the delay accordingly.