I'm trying to achieve the following:

Where:
Is this beyond the scope of the ASP.NET Validation Controls? The only solution I can think of is writing some bespoke javascript (for client side) and backing that up with some server side code.
One thing you can try is to have a CustomValidator(see here) check that both textboxes are not
empty. Then validate both textboxes with a regular expression. The expression should check for either a valid entry OR a blank field.
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