The 2026 high school baseball season is quickly approaching and as usual, excitement abounds throughout the state. Players and coaches have been working in preparation for the upcoming season, and, as is the case each year, there are some very talented players and teams across Florida.

Teams across the state have goals and aspirations to finish their seasons in the FHSAA state championships, but there is plenty of work to be done before that becomes reality. We hope to familiarize our readers with many of the teams across the state as we preview individual teams across Florida. We will take you right up to first pitch this season with these team previews and releasing our preseason top-25 rankings in the state.

Please keep checking back throughout the season as we will be your one-stop shop for everything related to high school baseball across the state.

Each week, we will be releasing our Players of the Week, as well as updating our Power 25 overall rankings.

*Please note the information has been gathered from head coaches across the state, based on their replies to the questionnaire we distributed over this offseason.

High School: Winter Park
Head Coach: Sid Cash
Classification: 7a
2025 Record (Finish): 25-6, lost in regional semi-finals (Won 25 games
Finished #5 in 7A, Isaac Incinelli 7A district 11 FACA player of the year, 5 players made all Metro team, 6 players made Orange County all-star game.)

 

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TOP RETURNING PLAYERS/TRANSFERS

Ryder Simon RHP 1B 2027
Pietro Pugliese OF 2026
Jackson Fleming OF 2027
Matthew Logan 1B 2026
Brendan Carbery P 2026
Miles Gotlib P 2026
Jackson Carney P 2027
Taiki Nikkuni P 2027

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TOP UNDERCLASSMEN

Massimo Mena INF. Bobby Welker INF Trey Hodges INF/OF/P

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OTHER UPPERCLASS FOLLOWS

Matt Logan 1B UCF commit
Pietro Pugliese OF Barry commit
Brendan Carbery P Montevallo commit
Taiki Nikkuni P Santa Fe College
Miles Gotlib P
Jackson Carney P

Ryder Simon P/INF. Miami commit
Jackson Fleming OF

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TEAM OUTLOOK

Projected Starting 9: C Dylan Malave. 1B Matt Logan. P Ryder Simon. 2B Rafael Gonzalez. SS Massimo Mena. 3B Bobby Welker. CF Jackson Fleming. RF Javier Carson. LF Pietro Pugliese
Projected Pitching Staff: Ryder Simon. Miles Gotlib. Brendan Carbery. Jackson CarneyTaiki Nikkuni
Team Strengths: Good core of players and good pitching staff

“The 2026 Wildcats hope to build on the success of the 2025 team. Winter Park always plays one of the toughest schedules in the state and this year is no exception. The 2026 schedule features 17 games against 2025 playoff teams. ” – Sid Cash, head coach

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Find more information on the 2026 Winter Park program below:

+ Follow them on X, Instagram, or Facebook: Wphsbaseball
+ Visit the Prep Baseball Florida, 2026 HS Team Previews

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FOLLOW PREP BASEBALL FLORIDA THROUGHOUT THE SPRING

+ Prep Baseball Florida on X
+ Prep Baseball Florida on Instagram
+ Prep Baseball Florida on Facebook

 

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Related Content

Upcoming Events

Showcase	State	Date	Location
Orlando Preseason ID	FL	12/29	The First Academy - Orlando, FL
Orlando Rising Stars ID (2030-2031 Grads)	FL	12/29	The First Academy - Orlando, FL
Jacksonville Preseason ID	FL	12/30	Bolles - Jacksonville, FL
Jacksonville Rising Stars ID (2030-2031 Grads)	FL	12/30	Bolles - Jacksonville, FL
Florida Preseason All-State (Invite-Only)	FL	01/04	IMG Academy - Bradenton, FL
Super 60 Pro Showcase	NATIONAL	02/01	The MAX - McCook, IL
Bradenton Rising Stars ID (2030-2031 Grads)	FL	02/08	IMG Academy - Bradenton, FL
Tampa Rising Stars ID (2030-2031 Grads)	FL	02/16	Berkeley Prep - Tampa, FL
South FL Rising Stars ID (2030-2031 Grads)	FL	03/17	Athletic Angels Field - Boynton Beach, FL
Florida Rising Stars Games (2030-2031 Grads)	FL	04/04	Jack Russell Stadium - Clearwater, FL