Why don’t the numbers on Form 1098-T equal the amounts I paid to Worsham during the year?

There are potentially many reasons for this discrepancy. 

First, the amount in Box 1 only represents amounts paid for qualified tuition and related expenses (QTRE) and does not include payments made for textbooks which, though important, are not considered mandatory education expenses for tax purposes. 

Secondly, Form 1098-T reports amounts that the student paid in a certain calendar year (which does not necessarily equal the amount that was invoiced during the calendar year). In addition, the pay date does not necessarily correspond to the dates that the classes were attended. For example, tuition for the Fall semester is typically billed in September so a student may have paid tuition for the Fall semester in January the following year so those payments would be represented in the student's following year 1098-T. The best and most accurate source of information about the amounts that you paid for qualified tuition and related expenses will be in the student ledger within the student portal.