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| Award | Year (↑) | Category | Nominee / Winner | Person |
|---|---|---|---|---|
| Cadet Award | 1999 | Outstanding Supporting Actress in a Drama Series | Nominee | Camryn Manheim |
| Cadet Award | 1999 | Outstanding Supporting Actress in a Drama Series | Winner | Kelli Williams |
| Electronic Media's Critics Poll | 1999.01 | Best Television Series (#1) | Winner | |
| Electronic Media's Critics Poll | 1999.07 | Best Television Series (#2) | Winner | |
| Online Television Academy Award | 2000 | Best Drama Series | Nominee | |
| Online Television Academy Award | 2000 | Best Lead Actor in a Drama Series | Nominee | Dylan McDermott |
| Golden Globe Award | 2000 | Outstanding Television Drama Series | Nominee | |
| Online Television Academy Award | 2000 | Best Supporting Actor in a Drama Series | Nominee | Michael Badalucco |
| Golden Globe Award | 2000 | Outstanding Actor in a Television Drama Series | Nominee | Dylan McDermott |
| Online Television Academy Award | 2000 | Best Supporting Actress in a Drama Series | Nominee | Lara Flynn Boyle |
| Online Television Academy Award | 2000 | Best Supporting Actress in a Drama Series | Nominee | Camryn Manheim |
| Online Television Academy Award | 2000 | Best Ensemble Cast in a Drama Series | Nominee | |
| E Pluribus Unum Award | 2000 | Television Drama Series | Nominee | |
| RATTY Award | 2000 | Best Supporting Actor in a Drama Series | Nominee | Steve Harris |
| PRISM Award | 2000 | Outstanding Multi-Episode Storyline in a Television Drama Series | Winner | |
| Cadet Award | 2000 | Outstanding Drama Series | Nominee | |
| Emmy Award | 2000 | Outstanding Casting for a Drama Series | Nominee | |
| RATTY Award | 2000 | Best Supporting Actress in a Drama Series | Nominee | Camryn Manheim |
| Viewers for Quality Television Award | 2000 | Best Actor in a Quality Drama Series | Nominee | Dylan McDermott |
| Online Television Academy Award | 2000 | Best Guest Actor in a Drama Series | Nominee | Paul Dooley |
| Online Television Academy Award | 2000 | Best Guest Actor in a Drama Series | Nominee | James Whitmore |
| Online Television Academy Award | 2000 | Best Guest Actor in a Drama Series | Nominee | Henry Winkler |
| Online Television Academy Award | 2000 | Best Guest Actress in a Drama Series | Nominee | Marlee Matlin |
| Online Television Academy Award | 2000 | Best Guest Actress in a Drama Series | Nominee | Beah Richards |
| Viewers for Quality Television Award | 2000 | Best Supporting Actor in a Quality Drama Series | Nominee | Michael Badalucco |
| Viewers for Quality Television Award | 2000 | Best Supporting Actor in a Quality Drama Series | Nominee | Steve Harris |
| Viewers for Quality Television Award | 2000 | Best Supporting Actress in a Quality Drama Series | Nominee | Camryn Manheim |
| Television Critics Association Award | 2000 | Outstanding Drama Series | Nominee | |
| Online Television Academy Award | 2000 | Best Direction in a Drama Series | Nominee | |
| RATTY Award | 2000 | Best Guest Actor in a Drama Series | Nominee | Henry Winkler |
| RATTY Award | 2000 | Best Guest Actor in a Drama Series | Nominee | James Whitmore |
| Viewers for Quality Television Award | 2000 | Best Quality Drama Series | Nominee | |
| Teen.com Entertainment Award | 2000 | Best TV Drama Series | Nominee | |
| Online Television Academy Award | 2000 | Best Writing in a Drama Series | Nominee | |
| Cadet Award | 2000 | Outstanding Supporting Actor in a Drama Series | Winner | Steve Harris |
| Golden Satellite Award | 2000 | Best Television Drama Series | Nominee | |
| Cadet Award | 2000 | Outstanding Supporting Actress in a Drama Series | Winner | Camryn Manheim |
| Golden Satellite Award | 2000 | Best Actor in a Television Drama Series | Nominee | Dylan McDermott |
| People's Choice Award | 2000 | Favorite Television Drama Series | Nominee | |
| Golden Satellite Award | 2000 | Best Actress in a Television Drama Series | Winner | Camryn Manheim |
| Golden Satellite Award | 2000 | Best Actress in a Television Drama Series | Nominee | Kelli Williams |
| RATTY Award | 2000 | Best Directing in a Drama Series | Nominee | Dwight Little, Dennis Smith |
| Cadet Award | 2000 | Outstanding Guest Actress in a Drama Series | Nominee | Marlee Matlin |
| Cadet Award | 2000 | Outstanding Guest Actress in a Drama Series | Winner | Beah Richards |
| Emmy Award | 2000 | Outstanding Supporting Actor in a Drama Series | Nominee | Michael Badalucco |
| Emmy Award | 2000 | Outstanding Supporting Actor in a Drama Series | Nominee | Steve Harris |
| NAACP Image Award | 2000 | Outstanding Drama Series | Nominee | |
| Screen Actors Guild Award | 2000 | Outstanding Performance by an Ensemble in a Television Drama Series | Nominee | |
| NAACP Image Award | 2000 | Outstanding Actor in a Drama Series | Nominee | Steve Harris |
| Emmy Award | 2000 | Outstanding Supporting Actress in a Drama Series | Nominee | Holland Taylor |
