20. Data Wins at Stratagema
Episode: Peak Performance (2.21)
One of a few moments on the list that isn’t a climax. After Crusher unwittingly saves the day again (heh, adults) to survive the Ferengi, Data accepts a rematch with Kolrami after he impossibly loses a game of Stratagema. It’s one of many points of character development for the android, who is beginning to learn how he can positively affect the humans around him.
19. Picard Goes Toe-To-Toe with Tomalak
Episode: The Defector (3.10)
This is probably my favorite Romulan moment ever in Star Trek, as they play a chess match in the Neutral Zone. Some delightful banter between the two captains.