This year's tournament, kicking of Thursday at 4 p.m., consists of five teams with the winner advancing to the Midwest Plains Regional Tournament in Wellington, Kan.
Michael Minner, coach of the Squirrels, likes his teams chances of keeping their streak alive.
"We feel like we have as good of a shot as anybody," he said. "We've won it three years in a row and we're hoping for four. Until somebody knocks us off we go in and approach it as we're the team to beat and that's the way that teams that come down here approach it.
"We're going to see everybody's best pitcher. They want to beat us so we're going to have to defend our home field."
Rounding out the rest of the field will be Jackson, Canton, Mineral Area and Booneville all looking for that one spot in regionals.
Charleston just wrapped up the regular season with a 19-14 mark after starting the season 0-5.
They will take on Kirksville in the second game of Friday's double-header with a scheduled start time of 7 p.m.
Though his team has it's ups and downs this season, Minner feels his team is peaking at the right moment.
"We've struggled a little bit this year throughout the season," he said. "But we feel like right now we're as solid as anybody on the mound and we can run anywhere from four to eight guys out there in starting roles.
"We feel like we're ready to see where we stand against these other teams in the state."
The Squirrels fate the rest of the tournament will depend on how they fair against Kirksville.
If Charleston wins they will go on to play Boonville Friday at 7 p.m. A loss to Kirksville would send the Squirrels to the loser's bracket where they would play the loser of Friday's Mineral Area vs. the winner of an earlier Canton/Jackson contest.
No matter what the Squirrels run in to this weekend, Minner feels there is nothing that a regular season that featured plenty of top-level teams couldn't prepare them for.
"We've faced tough teams where we've seen their good pitching," he said. "We feel like there is nothing that a team can throw at us this weekend that we haven't seen.
"How we react to that will be ultimately up to the kids."