Pictures:

This is the squash with the spots and then its leaves
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now the cucumbers: not sure if they are bugs eating it or a disease?
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I'm afraid your brown dots on your yellow squash might be pickleworm entry holes, which would mean that you have larvae in the squash. I had them in my spaghetti squash last year.

Not at all an expert though, so please google the pickleworm to confirm before you cut up your squash to check for larvae!

~emmers

Here is a link that might be useful: pickleworm damage

hmmmm. the spots don't look like holes per se. they look more like a dimple ya know? and they have a little something oozing from them.