I have a Red Oak that starts thousands of little acorns almost every year but never develop or drop off. Any ideas of why? I wish I took pictures of them, I do have a picture of the tree.
I am not an Oak Tree expert by any means but I know both Foragers Samuel Thayer & Arthur Haines know a lot about them & how to use them.
Could be poor pollination? but I really don’t know cuz I haven’t started studying Oaks yet.
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@stephane_rave maybe ?
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How old is your oak tree?
red oak acorns grow over 2 years. first year they are small and don’t change much in size, then grow larger and fall out of the 2nd year. Your oak seems a little young (before 30 years for an oak) so the first fructifications are a bit chaotic. Oak trees are able to self-pollinate ! 
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It’s definitely under 30 years old. Probably 20 at the most.
Imho it’s best to not dismiss lack of pollination yet.
Close cousin that is cultivated - chestnut tends to produce empty nuts when not pollinated. (Guides tend to recommend planting at least two.)