A CD155 will make more power than an IO-360 at 5000 feet. (lapse rate makes for only 25" MP at 5K) and the CD155 has a geared prop which generates more static thrust too. However your TSIO360 will still beat it everytime at 5K.
But further up, things change again. I'm not sure of the critical alt for the TSIO but it's possible that the CD155 may pull more HP at above ~20,000 than a TSIO360 as its not MP limited by vaporisation or detonation in the flight levels. Just a hunch.