The Owls slipped to 3-5 on the season after Tuesday night's three-point nonconference loss to the Indians at Anderson Arena.
William Woods University trailed 35-32 at halftime, but took a 71-69 lead on junior guard Shad Kimble's basket in the paint with 3 minutes, 2 seconds remaining in the game.
Haskell Indian Nations University (2-8) tied the contest when Macauley Brown made a pair of free throws with 2:42 to play. Brown then put the Indians in front 73-71 when he hit two more free throws with 2:23 left.
Junior guard Shamari Denson pulled the Owls even with a jumper in the lane with 1:07 to go. Haskell, though, took the lead for good at 76-73 on A'Ram Johnson's 3-pointer with :48 to play.
William Woods closed within 77-76 after senior guard DaShaun Stark converted 1-of-2 free throws with :15 remaining. Keith Moore then sealed the victory for the Indians by hitting two free throws with :10 to go.
Senior forward Darrien Dickey - who connected on 11-of-14 shots - produced a game-high 22 points to pace four players in double figures for the Owls. Denson and Stark chipped in with 14 points apiece, while junior forward Ray White contributed 11.
William Woods shot a torrid 53 percent (29-of-55) from the field, but was just 61 percent (11-of-18) from the foul line.
Dickey also pulled down a team-high nine rebounds as the Owls were edged on the boards 30-29.
Brown and Moore finished with 16 points apiece for Haskell, which shot 49 percent (27-of-55) as a team and 52 percent (13-of-25) from 3-point range. Johnson and Jimell Tate contributed 12 points apiece.
The Indians made 86 percent (12-of-14) of their free throws.
William Woods returns to American Midwest Conference play when it hosts Missouri Baptist University at 7:30 p.m. Thursday, Nov. 30.