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Do they need to be

  • Kashered?
  • Toiveled?

If yes to #1, how?

One potential issue with not kashering a corkscrew is that it could have had contact with non-kosher wine.

I'm not sure whether it would need to be toiveled, as I don't know well enough the details of what "directly involved in the preparation of food" means.

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    I liked the little illustration you had there :) – Y     e     z Mar 22 '16 at 3:42
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    @Yez I got worried people would downvote my question because of it. This site can be weird – SAH Mar 22 '16 at 3:43
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    I'll reproduce it here for the benefit of future readers: |--~~ – Y     e     z Mar 22 '16 at 3:52
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The Kof-K list of tevila instructions says that, according to the OU, Star-K and CRC, a corkscrew does not require tevilah because it does not touch the food. The Star-K confirms. And so does R Forst on behalf of OU.

Not clear why it would need to be kashered. The prohibition is on drinking non-kosher wine. If (1) the corkscrew is clean and (2) it was cold when it touched anything non-kosher then there is no issue. Remember that a corkscrew typically does not touch the wine at all which is the reason it doesn't require tvila. So washing the corkscrew well should remove any doubt.

As usual CYLOR and don't trust Internet strangers.

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The response of mbloch is perfect. I just want to quote 2 statements taken out from Gemara Avoda Zara 75B (I elided everything not directly concerned with the question)

‏1. כלי סעודה אמורין בפרשה‏[1]‏ ‏

‏ 2. דברים שנשתמש בהן ע''י צונן כגון כוסות וקתוניות וצלוחיות מדיחן ומטבילן והם טהורין‏[2]‏

[1] utensils connected with a meal (Soncino's translation).Rashi explains that from the verse that talk about "anything that comes into contact with fire" we learn that only dishes and cutlery are taken into account. The sentence ending is "then it will be purified" talks about Tevila in Kosher Mikve and immediately the purity is raised.
[2] Used ustensils used with cold meal simply need rinsing with water and Tvila.
So, corkscrews are not cutlery, and do not need Tevila; they may be in contact with cold wine, but only slightly, so at most should be washed.

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