Prep Baseball Report

MD 2026 Preseason Power 25: No. 9


Staff
Prep Baseball Maryland

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Over the next few weeks, leading up to the beginning of the 2026 MD High School season, our staff will be releasing our Preseason Power 25. This list will be comprised of public and private schools across the state that we feel have a strong chance of being successful in 2026.

#9 Chesapeake-AA Cougars 

Chesapeake fell just short of a 3A state title birth a year ago, and this roster in 2026 has all the makings to make a deep run once again. Possessing one of, if not the most talent-rich pitching staffs in the state, the Cougars will be able to match up with just about any lineup in the state and should be a ton of fun to watch all spring long. A perfect mix of experience, high-end velo and pitchability bodes well for this staff to find consistent success, and the return of some impact bats in the lineup provide nice balance on both sides of the ball.  

Key Players to Watch



Dakari Bailey

Class of 2027 / SS

Player Information

  • Graduating Class: 2027
  • Primary Position: SS
    Secondary Position: 2B
  • High School: Chesapeake High
    State: MD
  • Summer Team: Ole liners
  • Height: 6-1
    Weight: 178lbs
  • Bat/Throw: R/R




Dennis Bailey

Class of 2027 / OF

Player Information

  • Graduating Class: 2027
  • Primary Position: OF
    Secondary Position: OF
  • High School: Chesapeake High
    State: MD
  • Summer Team: Ole liners
  • Height: 6-0
    Weight: 165lbs
  • Bat/Throw: R/R




Matthew Sowers

Class of 2027 / RHP

Player Information

  • Graduating Class: 2027
  • Primary Position: RHP
    Secondary Position: SS
  • High School: Chesapeake High
    State: MD
  • Summer Team: Tides
  • Height: 6-2
    Weight: 195.8lbs
  • Bat/Throw: R/R




Cooper Barnes

Class of 2027 / RHP

Player Information

  • Graduating Class: 2027
  • Primary Position: RHP
    Secondary Position: 3B
  • High School: Chesapeake High
    State: MD
  • Summer Team: Dig In 17U National
  • Height: 5-11
    Weight: 165lbs
  • Bat/Throw: R/R




Dylan Adams

Class of 2026 / RHP

Player Information

  • Graduating Class: 2026
  • Primary Position: RHP
    Secondary Position: 1B
  • High School: Chesapeake-AA
    State: MD
  • Summer Team: Tides
  • Height: 5-11
    Weight: 215lbs
  • Bat/Throw: R/R