The season begins with the successful rescue of Data from the nineteenth century, and we learn just how long Guinan has actually known Picard. ("Time's Arrow")
Picard is temporarily assigned away from the Enterprise for a dangerous espionage mission against the Cardassians, but is captured and subjected to torture, nearly succumbing before being released ("Chain of Command"). Deanna Troi engaged in a similarly risky mission of espionage against the Romulans ("Face of the Enemy").
Picard also underwent significant personal development during this season. He formed an intense and troubled romantic relationship with the Enterprise's head of stellar cartography, Nella Daren ("Lessons"). After his artificial heart is nearly destroyed, Q helps Picard experience a vision of the unremarkable life he could have led, giving him a better understanding of his mortality and his reasons for living ("Tapestry").
Riker also experiences a deeply personal conflict, making a gripping personal battle with his own sanity ("Frame of Mind"), and later discovers an accidental transporter-copy of himself that had been abandoned on a desolate planet for nearly a decade ("Second Chances").
Several well-known recurring characters make appearances this season, the most famous among them being Montgomery Scott. The Enterprise engineer from the Original Series is discovered alive, and after an awkward period adjusting to the twenty-fourth century, sets out to explore the galaxy on his own ("Relics"). The sentient hologram Professor Moriarty returns, holding the ship captive in a complex game that he hopes will grant him freedom to live outside the holodeck ("Ship in a Bottle"). Reginald Barclay continues to develop, overcoming his fear of transporters ("Realm of Fear"). Q, in addition to his appearance in Picard's counterfactual vision, returns earlier in the season ("True Q").
We are left with the rediscovery of Lore, leading a group of rogue Borg, who with the influence of an emotional stimulant for androids, successfully seduced Data to become a willing participant in his violent plans in the cliffhanger that ends the season ("Descent").
The Enterprise crew follow Data to San Francisco of the 1890s. The crew deals with Samuel Clemens and runs into Jack London while trying to find a way to prevent aliens from interfering with 19th century Earth. Guest star: Jerry Hardin as Samuel Clemens.
The Enterprise investigates a vessel that crashed on the surface of a Dyson sphere 75 years ago. A pattern is found in the transporter buffer that turns out to be Montgomery Scott. He is released from the buffer and later agrees to return to the vessel with Geordi to help restore the logs. They become the only hope when the Enterprise is accidentally pulled inside the sphere. Guest Star: James Doohan as Montgomery Scott
A transporter malfunction turns Picard, Keiko, Ro and Guinan into children who become the ship's only hope when they are left aboard while the adult crew are forced to perform dangerous labor by Ferengi pirates.
Captain Jellico is assigned command of the Enterprise while Picard is sent on a covert mission into Cardassian territory. Guest star: Ronny Cox as Edward Jellico.
Barclay accidentally awakens Professor Moriarty on the holodeck who uses the powers at his disposal to coerce the crew into finding a way to allow him to leave the holodeck. Guest star: Daniel Davis as Professor Moriarty.
Worf is told on Deep Space Nine that his father is alive and is being held prisoner by the Romulans. Meanwhile an engineering experiment accidentally results in Data's first dream. Guest star: James Cromwell as Jaglom Shrek.
Picard tries to solve an ancient genetic mystery uncovered by his archaeological mentor and faces stiff competition. Guest star: Norman Lloyd as Richard Galen.
