The sentences that contain an example of contested usage are:
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The chair for the chair of the board of directors is at the head of the board table. - The term "chair" can be contested as it can refer to "chairperson" (gender-neutral) or "chairman" (gender-specific), which may lead to differing opinions on its usage.
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The postman needs to know who this letter is addressed to so it can be delivered. - The phrase "who this letter is addressed to" is often contested, as traditional grammar prescribes "to whom this letter is addressed" for formal usage while many people informally use the more conversational version.
These sentences illustrate instances where language use might be debated or where different grammatical standards may apply.