Bland, a repeat state qualifier will be competing in the 160-pound class against Smith-Cotton's Corey Witt (23-3).
Bland, a junior, has a record of 29-5.
He went 1-2 in state competition last year, with his only victory coming against Witt. Bland pinned Witt in 2:58 when they were both competing in the 152 class.
Madison, a junior competing in the heavyweight division, has a record of 26-6 and will be taking on Holt's Andrew Hammond (38-5).
This is Madison's first trip to the state meet.
Sikeston coach Chris Crosby says both his wrestlers have as good a shot as any at placing, but both are faced with difficult first-round opponents.
"It just depends on how we come out and wrestle," said Crosby.
"We've got opportunities, but at this level you never know. It's whoever is wrestling their best is going to move on."
Crosby thinks Bland's experience from last year gives him an advantage over a first-time qualifier.
"I think being up here last year will help him," said Crosby. "Any time you're on this type of stage, the experience is going to help you -- just competing in front of the big crowds and being in an arena like this."
Madison, similarly built to former Sikeston all-state wrestler Joe Johnson but significantly taller at 6-foot-2, has a similar demeanor to Johnson as well.
"He's so laid back, you can't really tell much with him," said Crosby. "He doesn't get real excited, he's just a laid-back kid. It really hasn't affected him yet. Once we get closer to the time for him to wrestle I'm sure the nerves and the excitement will build with him. Both of them have a goal to at least place at state. We'll just hope for the best."
Locally, Dexter's Mike Henley (26-7) will take on Marshall's Coldy Finnley (15-5) in the 112 class in Class 2. Also, Matt Overall (12-10) will wrestle Oak Grove's Tyler Russell (38-11).
In Class 1, DeAnton Brown (19-7) will wrestle Butler's Tim Sims (27-3) in the 171 class.
In heavyweight, D'Adrian Farr (12-10) will wrestle Versailles' Zach Monroe (11-4). In the 140 class, A.G. Sanders (15-12) will wrestle Ryan Mallen (29-7) of Cameron.