- Cover: Hit in the Heels, by Mike Stetson
- January: The Secret of Farpoint, by John M. Teska
- February: Bluejay 4, by Aurore de Blois
- John Christopher's F-104 breaking up in the USS Enterprise's tractor beam. (TOS episode: "Tomorrow is Yesterday")
- March: Neutral Zone, by José Perez
- April: Deployed, by Robert Bonchune
- An Aeroshuttle deploying from a ship above the USS Enterprise-D.
- May: Last Flight of the Columbia, by Pierre Drolet
- The wreckage of the starship Columbia (NX-02) on a desert world being surveyed by 24th century starfleet personnel. The Ships of the Line book puts this image in the DS9 chapter, and states that the Columbia had been discovered on a planet in the Gamma Quadrant.
- June: Farthest Star, by Daren Dochterman
- Center: Wolf 359, by Mojo
- The Battle of Wolf 359, prominently featuring a Constitution-class starship. This was the only image from this calendar not to be reprinted in the Ships of the Line book.
- An unusual starship above the USS Enterprise-D. The Ships of the Line book identifies the unusual new vessel as the USS Altair, an experimental prototype starship design.
- August: Plenty of Letters, by Gabriel Koerner
- A unique variation of a Constitution-class starship. The Ships of the Line book suggests this alternate Constitution-class design was one of the purposes refit schemes for the class, ultimately rejected in favour of the more familiar TOS movie-era design.
- September: Captain Arriving, a painting by Andrew Probert
- The Calypso returning to dock in the Enterprise-D.
- October: Armagossa Armageddon, by Koji Kuramura
- The USS Enterprise-D departing from the Armagosa observatory as it is destroyed by a shockwave. (TNG movie: Generations)
- November: Yesterday's Enterprise, by Alain Rivard
- The Enterprise-D facing off against a Klingon Bird-of-Prey as the USS Enterprise-C leaves to meet her fate. (TNG episode: "Yesterday's Enterprise").
- December: Solar Observation, by Fred Pienkos
- The USS Enterprise-D with Defiant-class and Intrepid-class starships above a star. The Ships of the Line books suggested all three of the pictured vessels are about to embark on a trip through time, simultaneously using the light-speed breakaway factor.
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