- This page is a comprehensive (and as much as possible, chronological) compilation of the women with whom James T. Kirk has had romantic entanglements (even briefly).
- "a new girl every week" in high school: (TOS novel: Best Destiny)
- Emily (surname unspecified), 2249: (TOS novel: Best Destiny)
- Ruth Cartwright, just before beginning at Starfleet Academy: (TOS episode: "Shore Leave"; TOS comic: "Starfleet Academy!")
- Elizabeth Shelby's great-great-great-grandmother. (NF novel: Being Human)
- Elizabeth Shelby's great-great-great-grandmother's sister. (NF novel: Being Human)
- Elizabeth Shelby's great-great-grandmother. (NF novel: Being Human)
- Unnamed blond lab technician, while at Starfleet Academy. Nearly married her: (TOS episode: "Where No Man Has Gone Before")
- It is possible that Carol Marcus and the blond lab technician are the same person.
- Janice Lester, at Academy or early, Starfleet career (mid-2250s): (TOS episode: "Turnabout Intruder")
- Carol Marcus, circa 2254 to 2260, gave birth to David Marcus in 2261: (TOS movie: Star Trek II: The Wrath of Khan; TOS comic: "Star-Crossed")
- Janet Wallace, circa 2261: (TOS episode: "The Deadly Years")
- Areel Shaw, circa 2263: (TOS episode: "Court Martial")
- Karen Hester-Jones, 3 years between 2261 and 2267 (TOS comic: "Experiment in Vengeance!")
- Andrea (android), 2266, Kirk makes advances to confuse her programming: (TOS episode: "What Are Little Girls Made Of?")
- Helen Noel, 2266: (TOS episode: "Dagger of the Mind")
- Kelinda: (TOS episode: "By Any Other Name")
- Eve McHuron: (TOS episode: "Mudd's Women")
- Nona: (TOS episode: "A Private Little War")
- Cortneelia, prior to 2268 (TOS video game: The Promethean Prophecy)
- Thalassa, (while using the body of Ann Mulhall): (TOS episode: "Return to Tomorrow")
- Deela: (TOS episode: "Wink of an Eye")
- Elaan: (TOS episode: "Elaan of Troyius")
- Marta, 2269, originally Captain Garth's "Orion girl", she switched loyalties: (TOS episode: "Whom Gods Destroy")
- Gilla Dupree, 2269: (TOS novel: Devil World)
- Miranda Jones, Kirk's charm in the end impressed her and gave her flowers before she left. (TOS episode: "Is There in Truth No Beauty?")
- Rayna Kapec (android), 2269, Kirk made advances-unintentionally confusing her programming: (TOS episode: "Requiem for Methuselah")
- Ola, a small, furry, naked creature from Lyra. In 2269, she was married to Kirk without his consent. (TOS novel: The Starless World)
- Captain Hunter, Kirk nearly group married her three times prior to 2270. (TOS novel: The Entropy Effect)
TOS, seasons 1-3 (to be filled in)
TAS (to be filled in)
- Lori Ciana, circa 2271: 1-year marriage contract: (TOS novelization: The Motion Picture)
- Gillian Taylor, briefly, in 2286: (TOS movie: Star Trek IV: The Voyage Home)
- R.J. Blaise in 2287 and 2290. (DC Comics second series))
- Martia, briefly in 2293: (TOS movie: Star Trek VI: The Undiscovered Country)