There have been periods in our own history where military technology declined. One of the times that most readily springs to mind is in the aftermath of the fall of Rome in the west...which is broadly speaking, a comparable era of history to the development level of Middle earth.
How one wishes to define military progress is of course up to the individual, however in the aftermath of the fall of Rome warfare on the whole became less structured, less organized and more poorly equipped.
Also note that for millennia of our history, again broadly speaking, the tools of the trade didn't change. Swords, spears, bows and various and sundry variations thereof were the tools of war until the advent of gunpowder.
I personally would have found it harder to swallow if Tolkein *had* described a world that had greatly advanced technologically, partially as a personal preference but also because our own development has taken so long.
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