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| Award | Year (↓) | Category | Nominee / Winner | Person |
|---|---|---|---|---|
| RATTY Award | 1999 | Best Drama Series | Winner | |
| NAACP Image Award | 1999 | Outstanding Actor in a Drama Series | Nominee | Steve Harris |
| Cadet Award | 1999 | Outstanding Writing in a Drama Series | Nominee | David E. Kelley |
| Online Television Academy Award | 1999 | Best Episode in a Drama Series | Winner | |
| Online Television Academy Award | 1999 | Best Episode in a Drama Series | Nominee | |
| Petcabus Award | 1999 | Best Supporting Actor in a Drama Series | Nominee | Michael Badalucco |
| Writers Guild Award | 1999 | Best Writing in an Episodic Drama Series for Television | Nominee | David E. Kelley |
| Petcabus Award | 1999 | Best Supporting Actor in a Drama Series | Nominee | Steve Harris |
| Viewers for Quality Television Award | 1999 | Best Actor in a Quality Drama Series | Nominee | Dylan McDermott |
| RATTY Award | 1999 | Best Lead Actor in a Drama Series | Nominee | Dylan McDermott |
| Cadet Award | 1999 | Outstanding Guest Actor in a Drama Series | Nominee | Tony Danza |
| Cadet Award | 1999 | Outstanding Guest Actor in a Drama Series | Winner | Michael Monks |
| Viewers for Quality Television Award | 1999 | Best Supporting Actress in a Quality Drama Series | Nominee | Kelli Williams |
| Cadet Award | 1999 | Outstanding Guest Actress in a Drama Series | Nominee | Linda Hunt |
| Viewers for Quality Television Award | 1999 | Best Supporting Actor in a Quality Drama Series | Nominee | Michael Badalucco |
| Petcabus Award | 1999 | Best Supporting Actress in a Drama Series | Winner | Camryn Manheim |
| Cadet Award | 1999 | Outstanding Guest Actress in a Drama Series | Nominee | Holland Taylor |
| RATTY Award | 1999 | Best Supporting Actor in a Drama Series | Nominee | Michael Badalucco |
| RATTY Award | 1999 | Best Supporting Actor in a Drama Series | Winner | Steve Harris |
| Emmy Award | 1999 | Outstanding Casting for a Series | Nominee | Janet Gilmore, Megan McConnell |
| RATTY Award | 1999 | Best Supporting Actress in a Drama Series | Nominee | Lara Flynn Boyle |
| RATTY Award | 1999 | Best Supporting Actress in a Drama Series | Winner | Camryn Manheim |
| Emmy Award | 1999 | Outstanding Cinematography for a Series | Nominee | Dennis Smith |
| RATTY Award | 1999 | Best Supporting Actress in a Drama Series | Nominee | Kelli Williams |
| Petcabus Award | 1999 | Best Ensemble Cast in a Drama Series | Nominee | |
| PRISM Award | 1999 | Outstanding Multi-Episode Storyline in a Television Drama Series | Winner | |
| Cadet Award | 1999 | Outstanding Sound | Nominee | |
| Emmy Award | 1999 | Outstanding Costuming for a Series | Nominee | |
| Cadet Award | 1999 | Outstanding Casting | Nominee | |
| RATTY Award | 1999 | Best Guest Actor in a Television Series | Nominee | Tony Danza |
| Online Television Academy Award | 1999 | Best Drama Series | Winner | |
| RATTY Award | 1999 | Best Guest Actor in a Television Series | Nominee | Michael Monks |
| RATTY Award | 1999 | Best Guest Actress in a Television Series | Nominee | Linda Hunt |
| Emmy Award | 1999 | Outstanding Drama Series | Winner | |
| RATTY Award | 1999 | Best Guest Actress in a Television Series | Winner | Holland Taylor |
| Television Critics Association Award | 1999 | Program of the Year | Nominee | |
| Banff Rockie Award | 1999 | Best Continuing Series | Nominee | |
| RATTY Award | 1999 | Best Writing in a Drama Series | Nominee | David E. Kelley |
| Television Critics Association Award | 1999 | Outstanding Drama Series | Nominee | |
| 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 |
