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I don’t think it’s that skirmishes were more or less likely in any time period, it’s that soldiers were trained to fight more for a particular type of warfare. For example, the Roman legionary was great in large battles between great blocks of troops. As a cohesive unit the century could dominate an equal or even greater number of opponents. What battles like the Teutoburg Forest massacre showed was when that cohesion was interrupted and the legionaries were forced to fight as individuals, that the training, the terrain and the man to man individualistic warfare gave the German tribes the advantage.
In the Dark Ages there are comparitively fewer large battles because the states required for massed combats don’t really exist, and forming a shieldwall becomes a big thing. The problem with shield walls is that they are very immobile. If you haven’t tried it (and any of us in law enforcement or the military will know,) getting even small groups of people to move together with riot shields takes practice, lots of practice. It’s common for novices to break up the formation just by being out of step with everyone else. Break up the cohesion and the shieldwall breaks and the combat becomes a skirmish. Without uniforms or heraldry it’s easy to imagine that killing a friendly in combat was a real possibilty.
By the age of gunpowder I think the big blocks of troops also compensated for the crappy accuracy of black powder weapons. They needed to throwout a wall of lead just to ensure they’d hit someone, thankfully the warfare of the day was to fght in large blocks of troops. I think this is why the Indian Wars in North America weren’t a slam duck for the Europeans. We would form firing blocks and they would encircle attacking from all sides and using terrain to break up the range advantage of firearms. Once the fighting changed to melee the club, sword, axe, knife and spear weilding native always held the advantage, whether Indians, Zulus, Maoris, Scots, etc.