Pitcher Jen-Ho Tseng was in the 2015 Bowman.
Dylan Cease was in 2016 Heritage Minors and 2017 Bowman.
Trevor Clifton was in 2017 Bowman.
Ian Happ is in the major leagues already and was in 2016's Bowman, Heritage Minors, and Pro Debut along with 2017 Bowman. There's a good chance he could end up in the flagship set's Update. Pro Debut and Update in the same year -- crazy!
Eloy Jimenez was in last year's Pro Debut and this year's Bowman.