if you just have the three month visa than no need to cancel. But if you have the extension of stay based on study you need to cancel before you go out. What is your nationality and place you stay in Thailand so we can advise you correctly which border you can use.
my observation: based on the definition we are lucky that transferwise is allowed. Based on the concept of transferwise no money is send between two countries, it is basily two local transfers. Someone put xyz amount in USD into an US account for a Thai account and someone puts xyz amount in THB into a Thai account for an US account. The job of transferwise is to balance it out. Correct me if I wrong.