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Awards: Cupid
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| Award (↑) | Year | Category | Nominee / Winner | Person |
|---|---|---|---|---|
| Electronic Media's Critics Poll | 1999.07 | Best Television Series (#14) | Winner | |
| Electronic Media's Critics Poll | 1999.01 | Best Television Series (#15) | Winner | |
| Online Television Academy Award | 1999 | Best New Drama Series | Nominee | |
| Online Television Academy Award | 1999 | Best Actor in a New Drama Series | Nominee | Jeremy Piven |
| Petcabus Award | 1999 | Best Actress in a Drama Series | Nominee | Paula Marshall |
| Petcabus Award | 1999 | Best Actor in a Drama Series | Nominee | Jeremy Piven |
| RATTY Award | 1999 | Best Drama Series | Nominee | |
| RATTY Award | 1999 | Best Lead Actor in a Drama Series | Winner | Jeremy Piven |
| RATTY Award | 1999 | Best Lead Actress in a Drama Series | Nominee | Paula Marshall |
| RATTY Award | 1999 | Best Writing in a Drama Series | Nominee | Rob Thomas |
| RATTY Award | 1999 | Best Directing in a Drama Series | Nominee | Scott Wynant |
| Salon's Best/Worst | 1998 | The Best Show of the Year | Winner | |
| TeeVee Award | 1999 | Best New Show | Winner | |
| TeeVee Award | 1999 | Best Hour Actor | Winner | Jeremy Piven |
| Television Critics Association Award | 1999 | Outstanding New Program of the Year | Nominee | |
| Young Artist Award | 2000 | Best Performance by a Young Performer Guest-Starring in a Television Comedy Series | Nominee | Joey Zimmerman |
| Youth in Film Award | 1999 | Best Performance by a Young Actress Guest-Starring in a Television Comedy Series | Winner | Anna Chumlsky |
