| Answer | Crossword Clue |
|---|---|
| FILLY | The 2009 Preakness winner, for one |
| HER | One-named winner of the 2021 Grammy for Song of the Year |
| BLACKEYEDSUSANS | Neckwear for a Preakness winner |
| TAYLORSWIFT | 2009 Grammy winner for "Fearless" |
| EMINEM | 2009 Grammy winner for "Relapse" |
| DERN | 2009 Golden Globe winner for "Recount" |
| BEHAR | Talk Show Emmy winner for 2009 |
| KANYEWEST | 2009 Grammy winner for "Swagga Like Us" |
| MRAZ | 2009 Grammy winner for "Make It Mine" |
| DRDRE | 2009 Grammy winner for "Crack a Bottle" |
| ADELE | 2009 Grammy winner for Best New Artist |
| DRE | 2009 Grammy winner for "Crack a Bottle," briefly |
| BEHAR | 2009 Emmy co-winner for Outstanding Talk Show Host |
