Index Match with wild card help

[rennerom]

I'm working on a project which provides two excel files. The first file, File1, contains a list of SKU descriptions under the header "SKU". They are somewhat long, and contain superfluous information.[TABLE="width: 139"]
<tbody>[TR]
[TD]SKU(A1)
[TABLE="width: 500"]
<tbody>[TR]
[TD]M GEL-CUMULUS 14[/TD]
[/TR]
[TR]
[TD]M GEL-CUMULUS 15[/TD]
[/TR]
[TR]
[TD]M GEL-CUMULUS 16 BR[/TD]
[/TR]
[TR]
[TD]W SUPERNOVA GLIDE 6[/TD]
[/TR]
[TR]
[TD]W SUPERNOVA GLIDE BO[/TD]
[/TR]
</tbody>[/TABLE]
[/TD]
[/TR]
</tbody>[/TABLE]
I have another file, File2, that contains more general descriptions under the header "Model", and provides dates when a model gets updated.

[TABLE="width: 500"]
<tbody>[TR]
[TD]Update(A1)[/TD]
[TD]Model(B1)[/TD]
[/TR]
[TR]
[TD]6/1/15[/TD]
[TD]Cumulus[/TD]
[/TR]
[TR]
[TD]9/1/15[/TD]
[TD]Glide[/TD]
[/TR]
</tbody>[/TABLE]


What I'm trying to do, is add the date from File2 to File1 in column B, based on the indexing the model names, and partially matching them to the SKU column from File1.

My first inkling was to index match with a wild card, but I can't seem to get anywhere.

=INDEX(File2.csv!A:A,MATCH(A2&"*",File2.csv!B:B,1))

Every time I try this, I only get 2 dates, and they're not correct. All other forms I've tried just yield N/A or Ref conflicts. Should I rename the the cells under Model to be a little closer to the SKU descriptions? Like GEL CUMULUS in stead of CUMULUS, or SUPERNOVA GLIDE instead of GLIDE. I don't need the gender qualifier (M/W) or model number (14, 15, etc...).