After entering the first 1098-T, you will be asked if the student attended another college. Answer yes and you will be allowed to enter the 2nd 1098-T. If both 1098-Ts are for the same school (that is unusual), then combine the amounts for each box and enter only one 1098-T.
Here's a post on the five main points on the 1098-T:
https://ttlc.intuit.com/community/college-education/discussion/i-need-help-with-1098t-section-colleg...
