The 285th issue of Doctor Who Magazine was released on 18 November 1999 and had a cover date of 15 December 1999. It advertised Mark Gatiss playing "the Doctor" in a Doctor Who spoof, The Web of Caves.
- A night to remember - Doctor Who theme night by Gary Gillatt and Andrew Pixley
- Everything you ever needed to know about...PROSE: Illegal Alien
- Thrilling adventures in Time and Space - Part Five Dog Days by Chris Howarth and Steve Lyons
- The Company of Thieves - Part Two
Profiles / Interviews
Reviews - 'Shelf Life'
- PROSE: Frontier Worlds
- Harlequin Miniatures: Doctor Who Miniatures
- REF: I, Who: The Unauthorised Guide to the Doctor Who Novels
- REF: The Doctor's Affect
- Slow Dazzle Worldwide: TARDIS and Dalek Desktop Calendars 2000
- Gallifrey Guardian
- Timelines (Letters)
- The Time Team - episodes 41 to 48 (The Reign of Terror episodes 5-6, Planet of Giants and The Dalek Invasion of Earth episodes 1-3)
- It's the end but...
- The DWM 285 Crossword (sponsored by BBC Books)
- Editor: Gary Gillatt & Alan Barnes
- Design: Peri Godbold
- Production: Mark Irvine
- Production Manager: Liz Teal
- Chief Sub: Jason Quinn
- Managing Editor: Alan O'Keefe
- Managing Director: Miles Stevens-Hoare
- This edition featured a competition in which readers could win the original DVD edition of the Five Doctors. The next issue would feature a review of this DVD.