In the sense of accumulated cruft, sure. Both Star Trek: TOS and OD&D are starting points, where everything is new and anything can happen. By the time of Wrath of Khan and AD&D, there's been a lot of thought about "the canon", which has taken on a life of its own. The Wrath of Khan specifically represents Star Trek taking something from its old lore and making something new from it. It's less obvious with AD&D, but you do have a lot of new material created as "fixes' or elaborations of old material. It becomes more obvious with later books, as people try to make spells and magic items and monsters to "fill gaps", especially in the planar cosmology. "If djinn are from the plane of Air, and efreet from the plane of Fire, what are the equivalent genie races for Water and Earth?"
This, however, means the OD&D supplements must be Season 3, and Holmes Basic is Star Trek the Motion Picture.
OD&D: Forbidden Planet, The Cage, Where No Man Has Gone Before, and The Corbomite Maneuver Greyhawk: Season 1 OD&D Supplements/Magazines/Judges Guild: Season 2 Basic Set/Monster Manual: Season 3 + The Animated Series Players Handbook: The Motion Picture Dungeon Masters Guide: The Wrath of Khan Unearthed Arcana: The Search for Spock Later AD&D Hardbacks: Movies 4-6 2e: The Next Generation
Because OD&D gives you all the building blocks, but it’s not yet distinctively TSR D&D. That comes in Season 1/Greyhawk. That’s where you get Romulans and Klingons and Khan and lots of other goodies; but they are just “episodes” still with no accumulation or sense of canon-building.