- 28 November 1999 - Help with endgames; Oops! Ruy Lopez
- 7 November 1999 - Getting started in chess; Lightning quick thinking; Offensive vs Defensive timesharing
- 31 October 1999 - How much practice? Pawns and castling; Opposite side castling
- 24 October 1999 - Choosing your stance; Piece strength; Goals of Lightning chess
- 10 October 1999 - What makes one GM better than another? The popularity of defense vs. offense; How long does it take to improve?
- 3 October 1999 - Kasparov vs. Fischer; How many openings must a chess player learn? Thoughts on Steinitz-von-Bardeleben 1895
- 26 September 1999 - How to develop a PLAN
- 19 September 1999 - Why do GMs draw? How much advantage to attack; The average US rating
- 5 September 1999 - When does the opening become the middlegame? Defending against strange openings
- 29 August 1999 - To attack or castle; Development as defense; When chess becomes more work than fun
- 15 August 1999 - Minimum material to checkmate; The evolution of chess; Combatting unorthodox openings
- 8 August 1999 - Playing your opponent; Basic Tactics
- 1 August 1999 - Global Opening (better than it looks!); A pawn is worth... what? I never play the middlegames I study!
- 25 July 1999 - Learning openings; Blitz = Bad? Finishing what you started
- 18 July 1999 - Correction to Puzzle 6; Sacrafices; Opposite-colored bishops
- 11 July 1999 - Too old to become a master? Playing vs Studying; Why Backstab breaks the rules
- 4 July 1999 - Answers to Chess puzzles; Well known vs obscure openings; Using initiative to attack
- 29 June 1999 - Chess puzzles
- 20 June 1999 - Free, strong chess computers; Opening with d3 or d4; Blindfold chess
- 13 June 1999 - What is en passant? Castling: o, O, or 0? Why don't GMs make money hand over fist?
- 6 June 1999 - Choosing a tutor; Worse development after just 10 moves
- 30 May 1999 - Studying is boring! Is it really worth it? The Jerome Gambit
- 9 May 1999 - Ethics of speed chess; Playing computers; King in the middle or guarding pawns?
- 2 May 1999 - What's good in a chess tutorial program; What good is chess anyway?
- 25 April 1999 - Gambits and the middlegame; 50-move rule; Responding to 1. e4
- 18 April 1999 - Best squares vs. best lines; Opposite-side castling; Play well now, play fast later
- 11 April 1999 - Is blitz chess bad for me? Mate now or later? Losing with King's Indian
- 4 April 1999 - Is my sacrafice worth it? Bishops vs Knights; King's Gambit for beginners
- 30 March 1999 - Unbalanced positions good for black? Algebraic notation; Moving a king in check; Facing d4
- 22 March 1999 - What's not a stalemate; Preparing for OTB tourneys
- 15 March 1999 - OTB vs Internet chess; When to sacrafice; Openings for beginners
- 8 March 1999 - The Torre Attack; Flagging; Getting to endgames without enough material
- 15 February 1999 - Opponent strength; Becoming World Champion; Sicilian variation
- 8 February 1999 - Black vs. White; The Colle; When to attack
- 1 February 1999 - Improving your rating when you're stuck
- 25 January 1999 - The best opening; The best endgame material