One great example where bad clock management actually worked out amazingly well was the 2005 Capitol One Bowl.
LSU vs. IOWA. Nick Saban's last game at LSU. Iowa trailed by 1 point with a minute and half left. Alll IOWA needs is a FG to win. Iowa completes a pass short of first down, then lines up to spike the ball but gets an illegal motion penalty. The Iowa QB Drew Tate does not know that the clock does not stop on an offensive penalty. The clock runs and runs while Iowa huddles, by the time the ball is hiked, it becomes obvious that it would be the last play of the game. So Iowa sends all 5 WR's deep (but not in hail mary formation) and Tate ends up throwing a 60 yard game winning TD on the last play of the game. The reciever caught the ball at the 15 and was almost tackled by the DB, but he kept his balance and made it to the end zone. The WR was a 5th year senior playing the last play of his career, and it was the first and only TD catch he ever had.
One reason the play worked out is LSU was not in prevent mode because their defense was set up to stop Iowa from getting in FG range, and did not substitute for a last second deep route. But really it was just dumb luck on Iowa's part.