Loser of the Year: Loser with the most ink.
Rookie of the Year: New Loser with the most ink, with less than two full Years since debut.
Most Imporved Loser: Loser with the most ink compared to his or her non-zero performance the previous Year.
Least Imporved Loser: Losers with the least ink compared to his or her non-zero performance the previous Year.
Top-Grossing Loser: Loser with the most ink.
Starting with Year 15, all of the above, except for Top-Grossing Loser, may be won only once.
| YEAR | LOSER OF THE YEAR | ROOKIE OF THE YEAR | MOST IMPORVED LOSER | LEAST IMPORVED LOSER | |
| 1 | Chuck Smith | -- | -- | -- | |
| 2 | Chuck Smith | Joseph Romm | Elden Carnahan | Tom Gearty | |
| 3 | Chuck Smith | Tommy Litz | Jennifer Hart | Elden Carnahan | |
| 4 | Jennifer Hart | David Genser | Jennifer Hart | Joseph Romm | |
| 5 | David Genser | Barry Blyveis | David Genser | Bob Sorensen | |
| 6 | Jennifer Hart | Ralph Scott | Brian Broadus | Russell Beland | |
| 7 | Jennifer Hart | Beth Baniszewski | Russell Beland | Barry Blyveis | |
| 8 | Jennifer Hart | James Pierce | Chris Doyle | Stephen Dudzik | |
| 9 | Russell Beland | Mark Young | Jean Sorensen | Meg Sullivan | |
| 10 | Chris Doyle | Milo Sauer | Chris Doyle | Russell Beland | |
| 11 | Russell Beland | Scott Campisi | Russell Beland | Seth Brown | |
| 12 | Russell Beland | Jon Reiser | Russell Beland | Milo Sauer | |
| 13 | Brendan Beary | Kevin Dopart | Brendan Beary | Chris Doyle | |
| 14 | Kevin Dopart | Jay Shuck | Ira Allen | Brendan Beary | TOP-GROSSING LOSER |
| 15 | Jay Shuck | Russ Taylor | Randy Lee | Tom Witte | Kevin Dopart |
| 16 | Beverley Sharp | Christopher Lamora | Jon Graft | Peter Metrinko | Kevin Dopart |
| 17 | Craig Dykstra | Craig Dykstra | Jeffrey Contompasis | Roy Ashley | Kevin Dopart |
| 18 | Jeffrey Contompasis | Gary Crockett | Craig Dykstra | Larry Yungk | Kevin Dopart |
| 19 | Gary Crockett | Nan Reiner | Michael Gips | Craig Dykstra | Kevin Dopart |
| 20 | Robert Schechter | Robert Schechter | Beverley Sharp | Judy Blanchard | Kevin Dopart |
| 21 | Danielle Nowlin | Danielle Nowlin | Frank Osen | Robert Schechter | Danielle Nowlin Chris Doyle |
| 22 | Frank Osen | Todd DeLap | Jeff Shirley | Danielle Nowlin | Chris Doyle |
| 23 | Mark Raffman | Amy Harris | Duncan Stevens | Frank Osen | Chris Doyle |
| 24 | Jesse Frankovich | John Hutchins | Jesse Frankovich | Kevin Dopart | Chris Doyle |
| 25 | Duncan Stevens | Dave Matuskey | Mark Raffman | Jon Gearhart | Jesse Frankovich |
| 26 | Tom Witte | Jon Ketzner | J. Larry Schott | Mark Raffman | Jesse Frankovich |
| 27 | Sam Mertens | Sam Mertens | Jonathen Jensen | Nan Reiner | Jesse Frankovich |
| 28 | Jonathan Jensen | Stephen "Potomac" Smith | Stephen "Potomac" Smith | Jesse Frankovich | Duncan Stevens |
| 29 | Frank Mann | Coleman Glenn | Jesse Frankovich | Stephen "Potomac" Smith | Jesse Frankovich |
| 30 | Karen Lambert | Karen Lambert | Pam Shermeyer | Eric Nelkin | Duncan Stevens |