These are really a pretty decent guess. There's nothing there that is anachronistic. But note that there's a variety of different soldiers represented, it's not just an average footsoldier through the ages. 1415 shows an archer's kit- and , clearly, that's because that's the year of Agincourt. 1485 has a full suit of expensive armor, perhaps so we can imagine Richard III staggering around in it, yelling for a horse.

An even more fun picture would be of included support personnel. The soldier of 1415 might have a wife, perhaps a servant, a spare horse, and be buying what he needed or looting it. Along with all the gear the 1944 soldier has, there are also all the cooks, drivers, trucks, planes, supply lines, communications gear that transport him, feed him, and tell him what to do. Those would be even more impressive contrasting piles.

The 1244 one strikes me as off in a few places.

The boots seem too tall, this is about the tallest I've seen boots in that period.

The helmet by 1244 should be more than just face protection, and should really be an early barrel helm like so.

Another two little niggles are the kite shield, when a Knight should really be using a heater (maybe they would take something bigger when fighting on foot, but that's nothing more than speculation) and the sword which looks very small, given that arming swords tended to have blades ranging from 28-31".

The last oddity there is the leather cuirass, which I imagine is based off this effigy at Pershore Abbey. But there's no hint that the cuirass in the photo is accurate, it seems a bit of a 're-enactorism'.

That's the only one I can pick apart at such a level though.

Edit: grammar fix

The 1066 one in particular seems to be based on the Saxons at the battle of Hastings. The Bayeux Tapestry seems to show them pretty consistently armed with a knee-length mail coat, conical helmet, kite shield, sword, and spear. In addition a handful of other weapons can be seen in use such as throwing axes, throwing maces, and the famous greataxe (the saxon on the far left can be seen carrying his greataxe in his shield hand, the one on the far right has discarded his shield and using his axe with two hands).

The Kite shield with a crusader cross on it 25 years before the first crusade seems a little suspect. But maybe it's just based off of an example I'm not familiar with.