In a back-and-forth game, Sikeston appeared to be in control with a 73-68 lead with a minute to go and possession of the basketball.
But a blocked shot by the Indians and back-to-back turnovers by the Bulldogs led to six straight points by North Side to get the lead, including two free throws by Maurice Taylor with 3.4 seconds remaining.
Sikeston inbounded the ball near midcourt and immediately called its final timeout with 3.1 seconds left.
After the timeout, Sikeston passed the ball in to junior guard Matt Ritch, who dribbled left and tried to find a teammate cutting to the goal, but the ball was tipped and went out of bounds as time expired.
"We were trying to get Matt the ball and cut Michael (Porter) to the bucket, but they got their hand on a pass and it went out of bounds as time expired," said Sikeston coach Gregg Holifield. "We had our chances, but couldn't pull the game out. It's a tough loss."
The Bulldogs' defensive problems continue to plague the team as North Side is the seventh team to hang at least 65 points in Sikeston's 10 games. Five of Sikeston's opponents have rung up over 70 points.
The athletic North Side team was unconscious from 3-point range, knocking down seven in the game.
"I think that my guards can shoot the ball exceptionally well, especially if we get set," said North Side coach Tony Brown. "If my guards can catch the ball I have confidence that they can knock down the 3."
Brighton, Sikeston's opponent in the first round on Thursday, canned six 3-
"The bottom line is we gave them too many looks in the first half and they got into a comfort zone," said Holifield. "Those teams shoot the basketball extremely well and they're quick. We have to get better on the defensive end."
Sikeston pretty much had its way on the offensive end themselves -- shooting 53 percent and scoring with somewhat ease in the paint -- but turnovers and poor ball-handling continue to haunt the Bulldogs.
Sikeston finished with 18 turnovers in the game, including two very costly turnovers in the final 30 seconds.
"We had a five-point lead with a minute to go and we just didn't take care of the basketball," said Holifield.
Sophomore forward Michael Porter did most of the damage, scoring 23 points with 18 rebounds, five assists, three steals and a pair of blocked shots.
"Our post players did not do a very good job on (Porter) at all," said Brown. "That kid is strong and very versatile. He can do it all. But at the very end I was just glad they couldn't get the ball to him."
A collapsing North Side defense tried to contain Porter in the fourth quarter, holding him to two points in the frame. But that allowed Bulldog senior Julian Beard to heat up as he scored 20 of his game-high 26 points in the second half, including 12 points in the action-packed fourth quarter.
"Michael really played well, but they started putting two and three people around him in the fourth quarter and that opened up opportunities for Julian and he stepped his game up," said Holifield.
While the loss is disappointing, dropping the team to 5-5, Holifield thinks playing the tough competition will only help his team improve.
"We're playing good teams right now and hopefully it will make us better down the stretch," said Holifield. "When you see good teams you can see your weaknesses and I think we can work on those things and get better."
Sikeston jumped out to an 8-0 lead to start the game and managed a 19-14 first quarter lead.
However, foul problems built up for the Bulldogs in the second quarter as North Side (6-8) rallied to take the lead heading into halftime at 40-37.
Sikeston regrouped its defense in the third quarter and grabbed a 56-55 lead heading into the fourth.
Twice Sikeston had three-point leads early in the fourth and both times North Side buried a 3-pointer to tie it.
North Side led by as much as 66-61 after another 3-pointer, but Sikeston rallied with a Beard 3-pointer, a Ritch baseline jumper and a Beard slam dunk to give the Bulldogs a 68-66 lead with three minutes left.
Sikeston opened up a 73-68 lead when Ritch his 1-of-2 free throws after coach Brown was whistled for a technical. But the Bulldogs couldn't hold on to the lead.
"Our defense finally stepped up at the very, very end," said Brown. "We put on a halfcourt trap just to throw off the offense and we got two quick steals."
North Side was led by Taylor's 19 points.
Bret Boylan had 18 points and Ryan Swift added 14 points.
Ritch added 11 points for Sikeston.
Sikeston played Munford in the seventh place game on Saturday. Results from that game will be in Tuesday's edition.