When two boats share the same hull type — in this case both the Contender 27 Tournament 2008 and the Contender 39 Tournament 2011 are deep vee designs with fiberglass construction — the buying decision usually comes down to a handful of practical questions: how many people are you putting on the water, how far do you trailer, and what does your tow vehicle weigh?

Size is the most obvious dividing line here. The Contender 39 Tournament 2011 measures 39,1 feet overall (2011), giving it roughly 10,1 additional feet of deck space compared to the Contender 27 Tournament 2008 at 29,0 feet (2008). Weight tells a clearer story for trailering families: the Contender 27 Tournament 2008 tips the scales at 545 lbs — 391 lbs more than the Contender 39 Tournament 2011 at 154 lbs. That difference is meaningful if you're working within a half-ton or three-quarter-ton truck's tow rating, especially once you factor in a motor, gear, and fuel.

The power gap is worth calling out. Rated to 1 400 hp, the Contender 39 Tournament 2011 has a 800-hp advantage over the Contender 27 Tournament 2008's 600-hp ceiling — enough to notice on acceleration and at cruising speed, particularly with a full passenger load. Fuel capacity breaks the other way: the Contender 27 Tournament 2008 carries 265 gallons versus 5 gallons in the Contender 39 Tournament 2011. On a lake day that's negligible, but for coastal cruising or long reservoir runs the extra range matters.

For family outings this is probably the sharpest distinction between the two. The Contender 39 Tournament 2011 is rated for 11 passengers, while the Contender 27 Tournament 2008 caps at 9. If you're regularly pulling extended family or a group of friends onto the water, the extra seats on the Contender 39 Tournament 2011 could be the deciding factor.