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Butch & Co.There are almost certainly earlier images of each of these guys that meet your criteria, and you didn't include board games or card games as qualifying for inclusion, but for what it's worth, here's what little we know...
Spalding appears on a circa 1870 CDV of Forest Citys.
Brouthers and Clarkson are both depicted on the box cover of The Champion Game of Base Ball, made by A S Schutz in 1889.
Comiskey is depicted on both the box cover and playing board of The World's Game of Base Ball, made by McLoughlin Brothers in 1889.
Davis, Delahanty ("Delehanty"), Ewing, Hamilton, McPhee, Nichols, Rusie, Thompson, Ward, and Young, as well as Brouthers and others, are all depicted on the playoing board of Zimmer's Base Ball Game, made by McLoughlin Brothers in 1893.
Baseball Games
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