After leading for the majority of the night -- including at the half and at the end of the third quarter -- the Falcons extended the Bulldogs' season-long drought to 16 straight losses and 21 in a row dating back to last year with a 50-49 win.
North Vermillion improved to 4-10 on the season.
Things looked bright for Union the majority of the night as they controlled the tempo in the paint at key times and managed to find multiple scoring sources.
Ethan Fettig and Ian Hamburg both drained 11 points, but it was a game-high 15 points from Austin Robertson that kept the Bulldogs hopes afloat for their first win.
Robertson helped Union to a decisive 26-18 edge on the glass. But down the stretch it was the UHS defense that once again spoiled their efforts.
After a double-digit lead in the first quarter turned into a 10-10 tie at the stop, the Bulldogs managed to surge ahead on both ends of the floor heading into the intermission.
They outscored North Vermillion 13-7 in the second frame and took what appeared to be a steady -- not safe, but steady -- 23-17 lead into the lockerroom.
But just as quickly as the pendulum swung the Bulldogs' way, it shifted back into the visitors grasp.
The Falcons whittled away at the margin and forged a tie at 32-all.
If not for easy baskets by Robertson on two of the last three Bulldog trips down the floor in the quarter, NVHS might have led.
His efforts in the closing seconds allowed a 3-pointer at the buzzer by North Vermillion's Braydon Woodard to cut the lead only to 36-35.
"Our post play was dominating on the offense and then defensively there was a little bit of lapse," Langley said about where his team stood entering the final stanza. "We were where we wanted to be, but were just unable to finish.
"We're going to have to work on handling the ball, making sure we don't throw it away and get a little better on our shot selection at critical times -- that's basketball in Indiana."
That wouldn't be the last time Woodard would deal a unsettling blow to Union's hopes.
"We couldn't stop Woodard from getting into where he was able to get his feet set and we were unable to contest the shots," Langley said. "He hit three 3-pointers in the second half.
"When we're hitting deuces and they're hitting treys, that will quickly hurt you -- it won't let you move forward."
After the two squads bounced the lead back and forth in the final eight minutes, Woodard drove the lane and drew a foul with five seconds to play.
His 1-of-2 successful attempts at the charity stripe snapped the last deadlock of the game at 49-all and left the Bulldogs with just over two seconds to respond.
After a timeout put the ball just shy of midcourt, a wide 3-pointer by Zac Birdsong bounced off the glass as time expired.
"We're still tired," Langley said. "At the end of the game we were blasted and every guy out there had worked their butts off.
"They just gave everything they had, but we've got to be able to finish on these kinds of games, we just let it slip through our fingers."
In the junior varsity contest a buzzer beating 3-pointer from Brayden Talley lifted the Bulldogs to a 38-35 win.
Talley was second on the scoresheet with 12 behind a game-high 13 by Melidian Maze.
Parker Lovelace added seven, Dakota Chesterfield four and Clay Figg two.
Union returns to action Friday when they travel to North Central for a Southwestern Indiana Athletic Conference contest.
NORTH VERMILLION (50) -- Kody Zumwalt 1-4 2-2 5, Devon Samms 1-1 0-2 2, Cody Wright 3-7 3-3 10, Braydon Woodard 5-12 2-7 15, Jacob Earl 3-3 3-3 10, Braeden Hollowell 1-1 0-0 3, Will Martin 1-3 2-2 5, Cory Davis 0-0 0-0 0, Levi Watson 0-0 0-0 0. Totals 15-31 12-19 50.
UNION (49) -- Ethan Fettig 5-10 1-4 11, Ian Hamburg 4-7 2-3 11, Austin Robertson 7-13 1-1 15, Zac Birdsong 1-5 0-0 2, Sterling Langley 3-5 2-3 8, Trey Bedwell 1-2 0-0 2, Brayden Talley 0-0 0-0 0. Totals 21-42 6-11 49.
North Vermillion 10 7 18 15 -- 50
Union 10 13 13 13 -- 49
3-point shooting -- North Vermillion 8-17 (Woodard 3-6, Zumwalt 1-2, Hollowell 1-1, Martin 1-3, Wright 1-4, Earl 1-1), Union 1-3 (Hamburg 1-1, Langley 0-1, Birdsong 0-1). Rebounds -- North Vermillion 18 (Zumwalt 5, Woodard 5), Union 26 (Fettig 9). Steals -- North Vermillion 9 (Wright 3), Union 8 (Fettig 4). Blocks -- North Vermillion 1 (Samms), Union 3 (Robertson 2). Turnovers -- North Vermillion 9, Union 13. Total fouls -- North Vermillion 7, Union 15. Fouled out -- Hamburg. Technical fouls -- none. Junior varsity -- Union 38, North Vermillion 35.