This year's tournament is being held at Notre Dame High School starting with Post 114's game Thursday and ending with a championship game Sunday, unless and additional tie-breaking game is needed Monday.
Jackson, Cape Girardeau and Dunklin County's Legion squad round out the rest of the tournament with Dunklin County holding the top seed.
Sikeston coach Chris Crosby likes his chances against opening up against the Express, a team Post 114 played in two close, but losing efforts this season.
"I think we have a good shot," Crosby said. "Both district games we played them we had them beat. Going in to the seventh inning we were there with a lead and just couldn't hold it.
"Hopefully our season-ending win against Jackson will give us the confidence that we can make those plays and I think we have a good shot at beating them."
Working in Sikeston's favor is two of their wins in this season's 5-18 campaign were against the second and third seeds in the tournament.
Post 114 got their first district win in two years when they beat second-seeded Cape Ford and Sons Post 63 3-2 in mid-June and wrapped up the regular season Monday with the above mentioned 4-3 decision over third-seeded Jackson Post 158.
Sikeston coach Matt Limbaugh likes the confidence that ending the season with a solid win brings to the team.
"That gives you momentum," he said. "You beat the number two-seed that tells you that anything is wide open if you play good ball.
"Just like against Jackson if we can sit there and make the plays defensively hopefully that key hit will come around that will at least keep us in the game and once you're in the game anything can happen."
If Post 114 comes away with the win Thursday, they will play first-seed Dunklin County Friday at 8 p.m. A loss against Post 158 will leave Sikeston playing the loser of Jackson vs. Cape on Saturday at 1 p.m.
Either way, after a rough season with a constantly changing line up, Limbaugh hopes his squad can end things on a high note.
"It's been a season where a lot of things just just haven't gone our way," he said. It's tough to have a successful year when you hope you have nine players dressed out when it's game time. You have to give credit to these boys who have stuck with it and want to play and want to try to represent Sikeston.
"Hopefully we can come out and make some noise. Come out jump out early on Bluff and hopefully end the season a little better than it's went all year."