No, if the output is a preamp out that is line level, a low to high impedance matching transformer will saturate way too early. The purpose of this kind of matching transformer is to step up mic level to line level (typically to -10dBu not +4dBu)
Without knowing which power amp, this question can't be answered accurately.
The scenario we're looking at is as follows:
I use a newly aquired Ampeg PF20T. This will drive my cabs as long as as it is strong enough.
Most of my perceived sound will be through IEM and I don't need too much juice in most scenarios.
When the 20 watts fail, a Guitar Sound Systems Baby Sumo amp comes into play.
I want to run one of the outputs of the ampeg into the Baby Sumo and one into FOH/IEM.
Right now I think that the output from the output transformer will be the one I use for FOH/IEM. It has the poweramp tube sound and sounds more lively to my ears. So that will be the one I want to send out for the audience and my earbuds. It will go into a behringer X32 or X-Air18, so I don't see a problem with the fact that this particular output is not very hot. The regular Line out would be the one to drive the GSS Baby Sumo.
I did experiment at home, by using a regular XLR cable and a Neutrik XLR to 1/4" TRS adapter.
This does not work for the output transformer outlet since the signal is too weak to drive the Baby Sumo. You can use it, but even with the volume all the way up, it is not much louder than running the Ampeg into the cab.
It does work fine with the regular preamp out. It gets loud.
But running a XLR cable into an XLR to 1/4" adapter creates a gigantic construct that does not look safe to my eyes when protruding from the power amp's front.