So you're not playing on "The Shadow of Death"? Well, you need to find the corresponding version to be on equal footing with everyone at the tournament.

Kamikaze meant something else.
In the early versions of Heroes, after hiring a hero in the tavern, the hero appeared with an army. In SoD (and 3.0 as well), this was removed. Subsequent heroes appear with 1 first-level warrior, but their first turn is calculated as if they have other warriors (second or third). If you get a Dess with a "non-existent" Orc, she will travel very little on the first turn (the speed of that Orc is taken into account).
And it seems you got a Dess without a "non-existent" Orc and she had faster warriors. That's why he traveled further.
Kamikaze, is this what you meant?