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I'm sorry, but Terlor's answer is incorrect. Note that I am counting the Generations of the first evolution.

Which generation has the most Pokemon which evolve by trading while holding an Item?

Gen 1: 9 (0 when counting the second evolution)

Poliwhirl -> Politoed (King's Rock)
Slowpoke -> Slowking (King's Rock)
Onix -> Steelix (Metal Coat)
Rhydon -> Rhyperior (Protector)
Seadra -> Kingdra (Dragon Scale)
Scyther -> Scizor (Metal Coat)
Electabuzz -> Electivire (Electrizer)
Magmar -> Magmortar (Magmarizer)
Porygon -> Porygon2 (Up-Grade)

Gen 2: 1 (6 when counting the second evolution)

Porygon2 -> Porygon-Z (Dubious Disc)

Gen 3: 4 (3 when counting the second evolution)

Feebas -> Milotic (Prism Scale)
Dusclops -> Dusknoir (Reaper Cloth)
Clamperl -> Huntail (Deepseatooth)
Clamperl -> Gorebyss (Deepseascale)

Gen 4: 0 (5 when counting the second evolution)

Gen 5: 0

Gen 6: 2

Spritzee -> Aromatisse (Sachet)
Swirlix -> Slurpuff (Whipped Dream)


So your answer would be Generation 1 if you count the traded Pokemon, and Generation 2 if you count the newly evolved Pokemon (the result).

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K den (filler)