Haha. It's your spreadsheet, so whatever's most useful to you should be the guiding criteria, not what I think. So I would ask yourself what you plan to do with this information once you have it. If knowing that there's at least one match for a given row is sufficient, then I'd just show the first hit. If you want to know what your options are for each row, then I'd show them all.
This formula will string together however many "hits" are identified in each row, separated by two spaces. It looks messier than it really is (the problem, as you discovered, is that vlookups only work with one input value, not a range). Does this work for you?
=IFERROR(" "&VLOOKUP(C2,Sheet1!$A$2:$B$419,1,0),"")&IFERROR(" "&VLOOKUP(D2,Sheet1!$A$2:$B$419,1,0),"")&IFERROR(" "&VLOOKUP(E2,Sheet1!$A$2:$B$419,1,0),"")&IFERROR(" "&VLOOKUP(F2,Sheet1!$A$2:$B$419,1,0),"")&IFERROR(" "&VLOOKUP(G2,Sheet1!$A$2:$B$419,1,0),"")&IFERROR(" "&VLOOKUP(H2,Sheet1!$A$2:$B$419,1,0),"")&IFERROR(" "&VLOOKUP(I2,Sheet1!$A$2:$B$419,1,0),"")&IFERROR(" "&VLOOKUP(J2,Sheet1!$A$2:$B$419,1,0),"")&IFERROR(" "&VLOOKUP(K2,Sheet1!$A$2:$B$419,1,0),"")
A variant of this (also messy) would be used to identify only the first hit.
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