User blog comment:Httyd big fan/Seventeenth Dragon Fight Club Match: Timberjack vs. Typhoomerang/@comment-24126950-20180404031440/@comment-24126950-20180404033619

All in all, it depends mostly on the intelligence of the Timberjack. If the Timberjack can exploit the Typhoomerang's weaknesses and/or time its abilities right, the Timberjack wins. However, the Typhoomerang is bigger, stronger, heavier, and is far more aggressive and territorial. Also, one attack from its Flaming Cyclone ability surely defeats the Timberjack.

Like with most (fair) battles, depends on who strikes first and on the individual's capacities.

However, if one must win, I personally think that after a long battle, the Typhoomerang would ultimately win. Why? Because the Typhoomerang is relentless and can apparently sustain several cut wounds in a fight (noted when Heather spoke of her first encounter with Windshear after the Razorwhip fought a Typhoomerang in Have Dragon Will Travel Part 2). It would also simply outfight the Timberjack, utilizing raw power and aggression.