Deadline to file Roth IRA Withdrawal for Tuition

I know I can use my Roth IRA to pay for my graduate program's tuition. My question is: if I first use my credit card/checking account to pay for tuition in 2020 fall, what is the deadline for me to transfer the same amount of money out of Roth IRA, and what is the deadline to file this withdrawal for tuition?

 

Thanks!