| 100% | DEREKJETER | 10 | Yankees shortstop (1995-2014) who was a first-ballot Hall of Famer but never won a season MVP award: 2 wds. |
| 86% | WADEBOGGS | 9 | Red Sox, Yankees, and Rays third baseman (1982-1999) who was a first-ballot Hall of Famer but never won a season MVP award: 2 wds. |
| 83% | TONYGWYNN | 9 | Padres outfielder (1982-2001) who was a first-ballot Hall of Famer but never won a season MVP award: 2 wds. |
| 82% | DAVIDORTIZ | 10 | Twins and Red Sox DH (1997-2016) who was a first-ballot Hall of Famer but never won a season MVP award: 2 wds. |
| 52% | ROBINYOUNT | 10 | Brewer Hall of Famer who won MVP awards as a shortstop (1982) and an outfielder (1989): 2 wds. |
| 52% | STANMUSIAL | 10 | Cardinal Hall of Famer who won MVP awards as an outfielder (1943, 1948) and a first baseman (1946): 2 wds. |
| 48% | JIMKELLY | 8 | Buffalo Bills quarterback who never won a Super Bowl but is in the Hall of Fame: 2 wds. |
| 48% | FRANTARKENTON | 13 | Minnesota Vikings quarterback who never won a Super Bowl but is in the Hall of Fame: 2 wds. |
| 47% | DANFOUTS | 8 | San Diego Chargers quarterback who never won a Super Bowl but is in the Pro Football Hall of Fame: 2 wds. |
| 44% | STEVENASH | 9 | Basketball Hall of Famer who was the first Canadian to win the NBA MVP award |
| 42% | ALEXRODRIGUEZ | 13 | Yankee player who won MVP awards as a shortstop (2003) and a third baseman (2005, 2007): 2 wds. |
| 40% | MIGUELCABRERA | 13 | First baseman who recently won his second consecutive A.L. MVP Award: 2 wds |
| 40% | CYNTHIACOOPER | 13 | Basketball Hall of Famer who was the very first MVP of the WNBA and MVP two times with the 31-Across (2 wds.) |
| 39% | JACKIESTILES | 12 | 2016 Women's Basketball Hall of Fame inductee who was the first Division I player to score over 1,000 points in a season: 2 wds. |
| 38% | SAMSMITH | 8 | "Stay With Me" singer who was a first-time Grammy nominee for Record of the Year (and won): 2 wds. |
| 38% | PAULMOLITOR | 11 | First MLB Hall of Famer who was primarily a DH |
| 37% | PETEROTOOLE | 11 | "Lawrence of Arabia" actor who was nominated for eight Oscars but never won one: 2 wds. |
| 37% | HONUSWAGNER | 11 | Pirates shortstop who was inducted in the first Baseball Hall of Fame ceremony in 1939: 2 wds. |
| 37% | LILLIANGISH | 11 | "The Birth of a Nation" star who is the only silent era actor to win the AFI Life Achievement Award: 2 wds. |
| 37% | SHERYLSWOOPES | 13 | Basketball Hall of Famer who was the WNBA's MVP three times with the 31-Across (2 wds.) |
| 37% | LISALESLIE | 10 | Basketball Hall of Fame inductee who was the first player to dunk in a WNBA game: 2 wds. |
| 36% | MICHAELJORDAN | 13 | Basketball Hall of Famer who was MVP of the 1993 NBA Finals (2 wds.) |
| 36% | SHERYLSWOOPES | 13 | Basketball Hall of Famer who was WNBA MVP three times (2000, 2002, 2005) (2 wds.) |
| 36% | LISALESLIE | 10 | Basketball Hall of Famer who was WNBA MVP three times (2001, 2004, 2006) (2 wds.) |
| 36% | LAURENJACKSON | 13 | Basketball Hall of Famer who was WNBA MVP three times (2003, 2007, 2010) (2 wds.) |
| 36% | ALTHEAGIBSON | 12 | Tennis great who was the first person of color to win a Wimbledon championship (2 wds.) |
| 36% | SPAHN | 5 | Baseball Hall of Famer Warren for whom a pitching award is named |
| 36% | TAYLORSWIFT | 11 | Multiple Grammy-winning singer-songwriter who is the first-ever recipient of Billboard's Woman of the Decade Award: 2 wds. |
| 36% | MIKEPIAZZA | 10 | Hall of Famer who won 11 Silver Slugger awards, the most of any catcher in MLB history (2 wds.) |
| 36% | DEREKJETER | 10 | Yankee shortstop who won the 1996 American League Rookie of the Year Award (2 wds.) |