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That was my very first computer war-game and I played in on an Atari 800. Yes, I am dating myself. When it was released for the Apple, it was touted as the most expensive war-game ever produced.

The oldest game I play on a regular basis (with my 13 year old grandson is the old Combat Mission x1 series (Beyond Overlord, Barbarossa to Berlin, and Afrika Corps).

ORIGINAL: Alex777

A few months ago I played a game of Computer Ambush (1981). Can't honestly say I enjoyed it though. The oldest I play regularly is Flight Commander II (1994).

Probably too new compared to these CGA / VGA games, but still enjoy playing Tacops.
and I'd argue that Anglo-German War, even though its relatively recent, looks about as old as it gets.
Reading this game list reminds me of all those times I had to edit himem.sys and tweak autoexec.bat files just to squeeze out a couple of kb to run aces over europe et.al.

Sega's PTO

Ah, autoexec.bat... you youngster! I bet you thought it tough to find 620kb... back in the day when spirits were brave, the stakes were high, men were real men, women were real women, and small furry creatures from Alpha Centauri were real small furry animals from Alpha Centauri we were getting by with 16, or a massive 48K!! And all dared to brave unknown terrors, to do mighty deeds, to boldly split infinitives that no man had split before - and thus was the Empire forged.

Don't Panic.

LOAD "" is where it is at

Not to mention having to regulate the header in C64 Datasette.

I just begun playing Ceasar 3 (98) again.