Well, you may or may not. I would expect there to be a slight, but appreciable, difference between the two. Usually, it's very subtle unless something's wrong.
I did a simlar test with an Outlaw 990 against the Benchmark DAC-1. Since the DAC-1 has a variable output, I was able to level match its output to the natural output of the Outlaw. I could then instantly switch between sources. IIRC, I used "bypass" mode for the DAC-1's input and "normal" mode for the DAC process in the Outlaw. Both the Outlaw and the DAC-1 were fed by a Denon DVD-1910 player.
I do believe I heard a difference in bass and soundstaging, with a nod to the DAC-1. It wasn't a huge difference, but I could hear it. Unfortunately, I had to return the DAC-1 before being able to have my wife do the switching for me in an effort at a blind test.
One other note -- be careful when using "bypass" mode on the 990 when using a sub and your mains are set to "small". The 990 incorrectly implements some type of high-pass filter at about 100 Hz. This is not only audible, but measurable as well. If you set your mains to "large," bypass mode works fine. This applies to "bypass" mode in the analog world only; "bypass" in the digital domain is OK. Outlaw is working on it...