Vlookup On Duplicate Fields with Multiple Values

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The problem with this is VLOOKUP will return the first match of the value every time. That is, for A it will match 2, B with 2, and C not at all. This is problematic since there are also values of 3 that could be matched for A as well. You could do something along the lines of "Match the second A in Spreadsheet 2", but there are an unequal number of As and Bs between Spreadsheet 1 and Spreadsheet 2.

A non-array method that may work more efficiently would be to insert this into the column next to your Spreadsheet 2 data:

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and drag down. You can hide this column later.

Then, try this in B5 and drag down:

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Again though, this is a little worrisome since the data to match ranges aren't the same.