Comment by Groxx

There is "wont" and "cant" but theyre rather rare nowadays. Probably others too, but Im (...im?) not able to remember any easily.

The closest I can think of thats maybe confusing is plurals vs possessive... but thats usually pretty clear from context, and when both are combined its often handled specially and thats weird but not usually confusing - English often has other in-sentence (and in-context) markers for plurality. You can of course construct ambiguous sentences, but thats true of many things that are accepted as "legal English".

It would be a shame to lose y'all'd've though.

https://www.merriam-webster.com/dictionary/wont

https://www.merriam-webster.com/dictionary/cant