I started in an online league when they were using OOTP3 (never bought the game...didn't even know about it). Just made lineup changes through email
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Joined a OOTP4 league and someone bought me the game for doing some logos for him.
Bought OOTP5. Loved it.
Skipped OOTP6.
Bought OOTP2007
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Three/Four clicks away from buying OOTP9.