Episodes:

Disc One:

• The Man Trap
  
• Charlie X
  
• Where No Man Has Gone Before
  
• The Naked Time

Disc Two:

• The Enemy Within
  
• Mudd's Women
  
• What Are Little Girls Made Of?
  
• Miri

Disc Three:

• Dagger of the Mind
  
• The Corbomite Maneuver
  
• The Menagerie (Part I)
  
• The Menagerie (Part II)

Disc Four:

• The Conscience of the King
  
• Balance of Terror
  
• Shore Leave
  
• The Galileo Seven

Disc Five:

• The Squire of Gothos
  
• Arena
  
• Tomorrow is Yesterday
  
• Court Martial

Disc Six:

• The Return of the Archons
  
• Space Seed
  
• A Taste of Armageddon
  
• This Side of Paradise

Disc Seven:

• The Devil in the Dark
  
• Errand of Mercy
  
• The Alternative Factor
  
• The City on the Edge of Forever

Disc Eight:

• Operation: Annihilate!

• Feature
  
• Preview trailers for each episode on that disc

Discs 1, 3 and 4 only:

• Feature
  
• Text Commentaries - Text Commentary on the 4 episodes are done by Michael Okuda and Denise Okuda - co-authors of The Star Trek Encyclopedia
  
• Text commentary on Where No Man Has Gone Before (disc 1), The Menagerie, Part 1 and Part 2 (disc 3), The Conscience of the King (disc 4)

Disc 8:

• Operation: Annihilate! preview trailer
  
• The Birth of a Timeless Legacy - This is the definitive telling of how it all began. Included are interviews with cast and network executives and producers. Features new interviews with Shatner, Nimoy, and Robert Justman.
  
• Life After Trek: William Shatner - We follow William Shatner around on his most current film and TV projects, charity events, conventions, trips, and hobbies including an exclusive invitation to his ranch to discuss his love of horses .
  
• To Boldly Go… Season One: - Cast members and production crew members recall fond memories/stories of working on the series. Includes intimate details about struggles behind the scenes and specific episodes - "The Naked Time", "City on the Edge of Forever", "Devil in the Dark", and "The Squire of Gothos".
  
• Reflections on Spock: - Leonard Nimoy discusses his character in depath, and explains why he chose to write two different books on the subject: "I Am Not Spock" and "I am Spock.".
  
• Kiss & Tell: Romance in the Final Frontier (24th CENTURY) - William Shatner, Leonard Nimoy, Walter Koenig and others take a fun look at the many romantic relationships seen on the series.
  
• Trek Connections Game - Instead of a regular "Trekker Trivia" style game, this "six degrees of Separation" text/photo featurette offers links between cast, crew, and guest stars to other films and tv shows, eventually circling back or ending on a TOS episode.
  
• Photo Log
  
• Sci-Fi Visionaries
  
• Kirk, Spock and Bones: Trek's Great Trio
  
• Envisioning the Final Frontier
  
• Sci-Fi Visionaries - A look at Star Trek's famous writers - Gene Coon, Harlan Ellison, George Clayton Thomas, Richard Matheson, D.C Fontana, and Roddenberry - featuring interviews with Trek Writers. New interviews with D.C Fontana, Bob Justman and John D.F Black