I only play short and casual games multiple times. Longer and harder maybe second time 10-20 years later. Always so much new games waiting.
Only exception is my favorite series: I've played Wing Commander around 40 times.
The expansions and WC2 and its expansions at least a dozen times,
WC3, WC: Prophecy & Secret Ops and Privateer 1&2 maybe half dozen.
Dragon Strike about 10 times.
First Monkey Island (as various versions) at least 20 times.
Some of the little old Master System games I've played at least 30 times: Rampage, Slap Shot, Snail Maze
Similarly in Fatal Racing (PC) I've played a 1½ hour series tens of times.
Strategy games can be hard to define what playing through means, unless there's a clear campaign. I've played a whole lot of Civilization 1, Master of Orion 1&2, Crush! Deluxe and some others.
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