| Winners | Delicate Steve | August 23, 2016 |
| For The Record (Single) | Beat Connection | August 5, 2016 |
| Justin Bieber at the Gates of Hell (Single) | So Much Light | July 14, 2016 |
| All Wet (Single) | Son Little | June 17, 2016 |
| case/lang/veirs | case/lang/veirs | Purchase June 17, 2016 |
| Black Terry Cat | Xenia Rubinos | Purchase June 3, 2016 |
| Kidsticks | Beth Orton | Purchase May 27, 2016 |
| The Party | Andy Shauf | May 20, 2016 |
| Prism Tats | Gary V | Purchase April 15, 2016 |
| Livin' On A High Note | Mavis Staples | Purchase February 19, 2016 |
| A Season On The Line | Glen Hansard | Purchase February 19, 2016 |
| The Psychedelic Swamp | Dr. Dog | Purchase February 5, 2016 |