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| Award | Year (↑) | Category | Nominee / Winner | Person |
|---|---|---|---|---|
| Emmy Award | 1999 | Outstanding Guest Actor in a Drama Series | Nominee | Tony Danza |
| Emmy Award | 1999 | Outstanding Guest Actor in a Drama Series | Winner | Edward Herrmann |
| Golden Globe Award | 1999 | Outstanding Television Drama Series | Winner | |
| Phlemmy Award | 1999 | Television Series | Winner | |
| Online Television Academy Award | 1999 | Best Lead Actor in a Drama Series | Winner | Dylan McDermott |
| Television Critics Association Award | 1999 | Outstanding Individual Achievement in a Drama Series | Nominee | Dylan McDermott |
| Television Critics Association Award | 1999 | Outstanding Individual Achievement in a Drama Series | Nominee | Camryn Manheim |
| RATTY Award | 1999 | Best Directing in a Drama Series | Nominee | Dwight Little |
| Online Television Academy Award | 1999 | Best Lead Actress in a Drama Series | Nominee | Lara Flynn Boyle |
| Golden Globe Award | 1999 | Outstanding Actor in a Television Drama Series | Winner | Dylan McDermott |
| Online Television Academy Award | 1999 | Best Supporting Actor in a Drama Series | Nominee | Michael Badalucco |
| Online Television Academy Award | 1999 | Best Supporting Actor in a Drama Series | Nominee | Steve Harris |
| Online Television Academy Award | 1999 | Best Supporting Actress in a Drama Series | Nominee | Camryn Manheim |
| Online Television Academy Award | 1999 | Best Supporting Actress in a Drama Series | Winner | Kelli Williams |
| Emmy Award | 1999 | Outstanding Lead Actor in a Drama Series | Nominee | Dylan McDermott |
| Television Critics Association Award | 1999 | Outstanding Individual Achievement in a Drama Series | Winner | David E. Kelley |
| Online Television Academy Award | 1999 | Best Ensemble Cast in a Drama Series | Winner | |
| Golden Globe Award | 1999 | Outstanding Supporting Actress in a Television Series, Miniseries or Made-for-TV Movie | Winner | Camryn Manheim |
| Golden Satellite Award | 1999 | Best Actor in a Television Drama Series | Nominee | Dylan McDermott |
| Online Television Academy Award | 1999 | Best Guest Actor in a Drama Series | Winner | Tony Danza |
| Online Television Academy Award | 1999 | Best Guest Actor in a Drama Series | Nominee | John Larroquette |
| Online Television Academy Award | 1999 | Best Guest Actor in a Drama Series | Nominee | Michael Monks |
| Online Television Academy Award | 1999 | Best Guest Actor in a Drama Series | Nominee | Rider Strong |
| Emmy Award | 1999 | Outstanding Sound Mixing for a Drama Series | Nominee | |
| Online Television Academy Award | 1999 | Best Guest Actress in a Drama Series | Nominee | Linda Hunt |
| Online Television Academy Award | 1999 | Best Guest Actress in a Drama Series | Winner | Holland Taylor |
| Screen Actors Guild Award | 1999 | Outstanding Performance by an Ensemble in a Television Drama Series | Nominee | |
| Emmy Award | 1999 | Outstanding Supporting Actor in a Drama Series | Nominee | Steve Harris |
| Emmy Award | 1999 | Outstanding Supporting Actor in a Drama Series | Winner | Michael Badalucco |
| Viewers Voice Award | 1999 | Favorite Hour-Long Series | Nominee | |
| Online Television Academy Award | 1999 | Best Direction in a Drama Series | Winner | |
| Peabody Award | 1999 | Winner | ||
| Emmy Award | 1999 | Outstanding Supporting Actress in a Drama Series | Winner | Holland Taylor |
| Viewers for Quality Television Award | 1999 | Best Quality Drama Series | Winner | |
| Emmy Award | 1999 | Outstanding Supporting Actress in a Drama Series | Nominee | Camryn Manheim |
| Publicists Guild | 1999 | Maxwell Weinberg Publicists Showmanship Award for Television | Winner | |
| Viewers Voice Award | 1999 | Favorite Actress in a Drama | Nominee | Camryn Manheim |
| Emmy Award | 1999 | Outstanding Supporting Actress in a Drama Series | Nominee | Lara Flynn Boyle |
| Online Television Academy Award | 1999 | Best Writing in a Drama Series | Winner | |
| Viewers Voice Award | 1999 | Favorite Actor in a Drama | Nominee | Dylan McDermott |
| Viewers for Quality Television Award | 1999 | Best Supporting Actor in a Quality Drama Series | Winner | Steve Harris |
| Viewers for Quality Television Award | 1999 | Best Supporting Actress in a Quality Drama Series | Winner | Camryn Manheim |
| Cadet Award | 1999 | Outstanding Drama Series | Nominee | |
| Online Television Academy Award | 1999 | Best Scoring in a Television Series | Nominee | |
| Cadet Award | 1999 | Outstanding Lead Actor in a Drama Series | Nominee | Dylan McDermott |
| Petcabus Award | 1999 | Best Drama Series | Nominee | |
| Online Television Academy Award | 1999 | Best Editing in a Television Series | Winner | |
| Online Television Academy Award | 1999 | Best Cinematography in a Series | Nominee | |
| Petcabus Award | 1999 | Best Actor in a Drama Series | Nominee | Dylan McDermott |
| Cadet Award | 1999 | Outstanding Supporting Actor in a Drama Series | Nominee | Steve Harris |
