Sikeston upset favored Charleston with 31.5 points to the Bluejays' 28.5 points to take the title.
Both teams advance to sectional play. Sikeston will play John Burroughs in St. Louis next Saturday.
Sikeston had three individuals qualify for the state tournament. In doubles, Peter Jones and Chris Robey took first place with a 6-2, 7-5 victory over Charleston's Blake Branum and Lee Hess.
Also, Sikeston singles player Marc Leible took second place after defaulting to Charleston's Alec Peterson in the championship match due to illness.
"It was an excellent day for us," said Sikeston head coach Brian James. "Every single entry we had probably played up to their abilities. Peter and Chris had a goal of winning it this year and they had a good day and a tough finals match. They defeated the fourth place state doubles team from last year in Branum and Hess."
While Leible didn't take first, the district championship was weighing in the balance with his semifinal match against Charleston's Derek Hoppe.
Leible won the marathon match 6-4, 6-7, 7-6. The match was so exhausting that neither Leible or Hoppe were able to continue to their next matches.
"His match with Derek Hoppe is one of the most grueling matches I've ever seen," said James. "They had two different tiebreakers in the second and third set. Basically the team championship hinged on that match. Both of them showed a lot of guts. They were just spent after that incredible semifinal match that neither one of them had anything left. But both of them have a lot to be proud of. It was certainly the most memorable match of the day."
Sikeston also got a huge day out of the unseeded doubles team of Kyle Weeks and freshman Sam Zhao, who made it all the way to the semifinals before settling for third place.
The two knocked off two higher seeded teams before falling to Branum and Hess 6-2, 6-1.
"I can't say enough about Sam Zhao and Kyle Weeks -- they were just tremendous today," said James. "They pulled out two very tough matches against two seeded opponents and made it all the way to the semifinals and earned big team points for us. They just had an outstanding day."
Sikeston's Chris Matthews also competed but had a tough draw with top-seeded Peterson after a first round bye.
Peterson defeated Matthews 6-0, 6-0.
"Chris Matthews had the tough draw in singles and drew Peterson right off the bat so he just didn't have a chance to show what he could do," said James. "Peterson's just outstanding and a tough, tough player."
Jones and Robey started off by defeating Charleston's Jake Garrard and Drew Kemp 6-0, 6-2. They then defeated Walton and Slabby of Crystal City 6-0, 6-0 and followed that up with a 6-2, 6-2 win against Dexter's James Ford and Ben Smith.
On a day that saw heavy rains, the tournament had to be relocated to Cape Girardeau.
"We had a lot going on with this district," said James. "The weather forced us up to Cape and Cape Central was nice enough to let us use their courts. We were lucky enough to get it in before it rained and got too dark."
Sikeston entered the district as perhaps the second favorite behind Charleston, which had defeated the Bulldogs twice during the regular season in dual matches.
But a lineup shift just one week prior may have been the difference in the championship and second place.
"I thought we were good enough to place in the top two, but I thought beating Charleston would be pretty tough because they handled us twice in the dual meets," said James. "I didn't know that we matched up that well with them. But we had a doubles team kind of come out of nowhere in Sam and Kyle.
They hadn't played together all year and then about the last week I matched them up and they really seemed to click. They were the difference in the day because they gave us some points that I didn't really expect two or three weeks ago. The kids were very excited and I was excited for them. We had some ups and downs this year -- our record was pretty good -- but I wasn't sure we played that great at all times. But today everything came together. It was a fun day for us.
Other teams that finished in the top five in the district were Dexter (3rd place: 18.5), St. Pius X (4th: 16.5) and Kennett (5th: 13). Arcadia Valley, Festus, Crystal City, Potosi, Park Hills Central, North County and DeSoto also competed.