Yes, if you have more than one row of entries in box 14 on your W-2, you should add each line for box 14 in your W-2 information in TurboTax.
Just enter the description and amounts as is on your W-2 form and then select "+ add another row" for box 14 for each line until you are finished.
See screenshot example for adding another box 14 row to your TurboTax W-2 entry.
