(*): W=Win, N=Nomination
| Year | * | Category | Works | Shared |
|---|---|---|---|---|
| 1999 | N | Best Performance by an Actor in a Leading Role | Shakespeare in Love (1998) | - |
| Year | * | Category | Works | Shared |
|---|---|---|---|---|
| 1999 | W | Favorite Male Newcomer | Shakespeare in Love (1998) | - |
| Year | * | Category | Works | Shared |
|---|---|---|---|---|
| 1999 | W | Breakthrough Artist | Elizabeth (1998) | - |
| Year | * | Category | Works | Shared |
|---|---|---|---|---|
| 1999 | W | Most Promising Actor | Shakespeare in Love (1998) | - |
| Year | * | Category | Works | Shared |
|---|---|---|---|---|
| 1998 | W | Most Promising Actor | Shakespeare in Love (1998) | - |
| Year | * | Category | Works | Shared |
|---|---|---|---|---|
| 2019 | N | Best Villain | The Handmaid's Tale (2017) (TV) | - |
| Year | * | Category | Works | Shared |
|---|---|---|---|---|
| 1999 | W | Best Kiss | Shakespeare in Love (1998) | Gwyneth Paltrow |
| 1999 | N | Best Breakthrough Male Performance | Shakespeare in Love (1998) | - |
| Year | * | Category | Works | Shared |
|---|---|---|---|---|
| 2018 | N | Outstanding Supporting Actor in a Drama Series | The Handmaid's Tale (2017) (TV) | - |
| Year | * | Category | Works | Shared |
|---|---|---|---|---|
| 2005 | N | Best Actor in a Supporting Role, Comedy or Musical | The Merchant of Venice (2004) | - |
| Year | * | Category | Works | Shared |
|---|---|---|---|---|
| 2019 | N | Outstanding Performance by a Male Actor in a Drama Series | The Handmaid's Tale (2017) (TV) | - |
| 2018 | N | Outstanding Performance by an Ensemble in a Drama Series | The Handmaid's Tale (2017) (TV) | Elisabeth Moss, Yvonne Strahovski, Samira Wiley |
| 1999 | W | Outstanding Performance by a Cast | Shakespeare in Love (1998) | Ben Affleck, Simon Callow, Jim Carter |
| 1999 | N | Outstanding Performance by a Male Actor in a Leading Role | Shakespeare in Love (1998) | - |
| Year | * | Category | Works | Shared |
|---|---|---|---|---|
| 1999 | N | Film - Sexiest Love Scene | Shakespeare in Love (1998) | Gwyneth Paltrow |
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