| 100% | TITO | 4 | Two-time A.L. Manager of the Year Francona, familiarly |
| 59% | PENA | 4 | 2003 A.L. Manager of the Year Tony |
| 56% | TORRE | 5 | Joe who was twice A.L. Manager of the Year |
| 51% | PENA | 4 | Tony who was the 2003 A.L. Manager of the Year |
| 51% | NIXON | 5 | Two-time Time Man of the Year (and a hint to 17-, 27-, 41- and 54-Across) |
| 50% | DUSTYBAKER | 10 | N.L. Manager of the Year, 1993, 1997 and 2000 |
| 48% | CMA | 3 | Group that has named Garth Brooks its Entertainer of the Year a record seven times: Abbr. |
| 48% | LOU | 3 | Three-time MLB Manager of the Year Piniella |
| 48% | LARUSSA | 7 | Four-time MLB Manager of the Year Tony |
| 47% | NOVAKDJOKOVIC | 13 | Serbian tennis star who's been ATP Player of the Year a record eight times: 2 wds. |
| 47% | BOWA | 4 | Larry __, former Phillies All-Star shortstop who was 2001 N.L. Manager of the Year |
| 46% | ALOU | 4 | 1994 NL Manager of the Year Felipe |
| 45% | OBAMA | 5 | Two-time Time magazine Person of the Year |
| 45% | ALOU | 4 | 1994 National League Manager of the Year Felipe |
| 45% | SEASONAL | 8 | Occurring at a particular time of the year |
| 45% | JETER | 5 | 1996 A.L. Rookie of the Year |
| 45% | DEREKJETER | 10 | 1996 A.L. Rookie of the Year |
| 45% | AGEE | 4 | 1966 A.L. Rookie of the Year |
| 45% | FISK | 4 | 1972 A.L. Rookie of the Year |
| 45% | RIPKEN | 6 | 1982 A.L. Rookie of the Year |
| 45% | ALOMAR | 6 | 1990 A.L. Rookie of the Year |
| 45% | JOEMADDON | 9 | Three-time Manager of the Year who coached the team to victory: 2 wds. |
| 44% | BELTRAN | 7 | 1999 A.L. Rookie of the Year Carlos |
| 44% | LYNN | 4 | 1975 A.L. Rookie of the Year Fred |
| 44% | DUSTYBAKER | 10 | Three-time National League Manager of the Year whose surname suggests cookies and cakes (2 wds.) |
| 44% | BIANNUALLY | 10 | Happening two times a year |
| 44% | JEANNEDIELMAN | 13 | Film voted the greatest of all time in a prominent 2022 critics’ poll, familiarly |
| 44% | ROCCO | 5 | Baldelli who was AL Manager of the Year in 2019 |
| 44% | SEASON | 6 | Time of the year |
| 43% | ELS | 3 | P.G.A. Tour Rookie of the Year two years before Woods |