Do I enter a 2019 tuition payment cleared in 2020 on 2019 taxes?

Please see this answer from DDollar:

t sounds like you were reimbursed under an Accountable Plan. If that is correct, you do not need to do anything.  According to the IRS:

How you treat reimbursements depends on the arrangement you have with your employer.

There are two basic types of reimbursement arrangements—accountable plans and no-naccountable plans. You can tell the type of plan you are reimbursed under by the way the reimbursement is reported on your Form W-2.

To be an accountable plan, your employer's reimbursement arrangement must require you to meet all three of the following rules.

• Your expenses must have a business connection. This means your expenses must be deductible under the rules for qualifying work-related education explained earlier.

• You must adequately account to your employer for your expenses within a reasonable period of time.

• You must return any reimbursement or allowance in excess of the expenses accounted for within a reasonable period of time.

If you are reimbursed under an accountable plan, your employer shouldn't include any reimbursement of income on your Form W-2, box 1.

Non-accountable Plans

Your employer will combine the amount of any reimbursement or other expense allowance paid to you under a non-accountable plan with your wages, salary, or other pay and report the total on your Form W-2, box 1.

You can deduct your expenses regardless of whether they are more than, less than, or equal to your reimbursement.