H1b transfer to full time student (F1), then get sponsor again (H1b) after one/two semester?

Hello everyone,

I’m holding H1b visa for two years and still in active. I would like to pursue a different master program within US (F1 visa) and not sure if I will need to do the lottery procedure again once I get sponsor by another company for H1b visa after graduation ( or maybe in the middle of study program)? Thank you for your answer!