| 2008/2009 Theatre Arts Guild Award Winners | CW Staff | Theater |
| Cover Story: About Face(book) | Sean Brennan | Other |
| Dining: Brunch Munch | Dave Link | Dining |
| Film: Everybody Hurts | Julien R. Fielding | Film |
| Hemline | Lindsey Baker | Style |
| Kathman's TV Review: “Merlin” | Ryan Kathman | Other |
| Law-Talking Guy Has a Ball | Patrick Runge | Columnists |
| Local Tunes | Marq Manner | Columnists |
| Meeting the Band: The Box Elders | Chris Aponick | Music |
| Mike Fratt | Mike Fratt | Columnists |
| Music: Simon Says | Will Simons | Music |
| New of the Weird | Chuck Shepherd | Other |
| Nightlife: Our Very Own Tom Cruise | Chris Aponick | Nightlife |
| Sports: Heavy Stuff | John Fey | Sports |
| Style: Getting the Itch | Lindsey Baker | Style |
| TAG Awards: Bat (Blank) Crazy! | David Williams | Theater |
| Wine Notes | John Fischer | Columnists |
