| 12/6/2018 | Thu | Board Meeting (Dec) | 5:30pm to 6:30pm |
| 1/2/2019 | Wed | Spring Online Registration Begins | |
| 1/3/2019 | Thu | Board Meeting (Jan) | 5:30pm to 6:30pm |
| 1/30/2019 | Wed | Walk In Registration Preparation | 6pm to 8pm |
| 1/31/2019 | Thu | Wicomico County Good Sport Award Banquet | 5:30pm |
| 2/2/2019 | Sat | Walk In Registration at Field House | 9am to Noon |
| 2/7/2019 | Thu | Board Meeting (Feb) | 5:30pm to 6:30pm |
| 2/7/2019 | Thu | PIC Training after Board Meeting | 6:30pm |
| 2/9/2019 | Sat | Walk In Registration at Field House | 9am to Noon |
| 2/16/2019 | Sat | Walk In Registration at Field House | 9am to Noon |
| 2/23/2019 | Sat | Walk In Registration at Field House | 9am to Noon |
| 2/23/2019 | Sat | Bat Demo Day | |
| 2/27/2019 | Wed | Walk In Registration at Field House | 6pm to 8pm |
| 3/2 - 3/3/2019 | Sat/Sun | 20% off at Dick's | |
| 3/4/2019 | Mon | Chipotle Fundraiser | 4pm to 8pm |
| 3/7/2019 | Thu | Board Meeting (Mar) | 5:30pm to 6:30pm |
| 3/7/2019 | Thu | Teams & Managers decided (Majors & Minors) | 6:30pm to 8:30pm |
| 3/9/2019 | Sat | Assessments (Crown) (Majors 9am & Minors 10am) | 9am to 11am |
| 3/10/2019 | Sun | Draft (Majors & Minors) | 4:30pm-7:30pm |
| 3/10/2019 | Sun | Daylight Savings Time Starts | |
| 3/11/2019 | Mon | Team Intros/Emails/Meetings (Majors & Minors) | |
| 3/12/2019 | Tue | Practices Begin (Majors & Minors) | |
| 3/16/2019 | Sat | PM Assessments (More Info Here) | 9am to 11am |
| 3/16/2019 | Sat | Finalize PM & TB Teams | |
| 3/16/2019 | Sat | Tournament | |
| 3/17/2019 | Sun | Tournament | |
| 3/18/2019 | Mon | Order Uniforms | |
| 3/18/2019 | Mon | Team Intros/Emails/Meetings (PM & TB) | |
| 3/19/2019 | Tue | Practices Begin (PM & TB) | |
| | Chipotle Fundraiser 4-8pm | |
| 3/23/2019 | Sat | Finalize Int, Jr & Sr Teams | |
| 3/23/2019 | Sat | Tournament | |
| 3/24/2019 | Sun | Tournament | |
| 3/25/2019 | Mon | Team Intros/Emails/Meetings (Int, Jr & Sr) | |
| 3/26/2019 | Tue | Practice Begins (Int, Jr & Sr) | |
| 3/27/2019 | Wed | Team Parent Meeting | 6pm |
| 3/29/2019 | Fri | Post Game Schedule & PIC Schedule on website | |
| 4/4/2019 | Thurs | Board Meeting (Apr) | 5:30pm-6:30pm |
| 4/7/2019 | Sun | Manager Meeting - Safety & Umpire Training | TBD |
| 4/8/2019 | Mon | Pick Up Uniforms from Vendor | |
| 4/9/2019 | Tue | Distribute Uniforms to players | |
| 4/12/2019 | Fri | Clean-Up Day in preparation for Opening Day | |
| 4/13/2019 | Sat | Opening Day | |
| 4/14/2019 | Sun | Opening Day (Backup-Ceremony & Games Only) | |
| 4/15-5/31/2019 | | Spring Season Games | |
| 4/21/2019 | Sun | Easter Sunday | |
| 5/2/2019 | Thu | Board Meeting (May) | 5:30pm to 6:30pm |
| 5/4/2019 | Sat | Tournament | |
| 5/5/2019 | Sun | Tournament | |
| 5/11/2019 | Sat | FLL Night at Shorebirds | 7:05pm |
| 5/12/2019 | Sun | Mother's Day | |
| 5/18/2019 | Sat | Tournament | |
| 5/19/2019 | Sun | Tournament | |
| 5/25/2019 | Sat | Tournament | |
| 5/26/2019 | Sun | Tournament | |
| 5/27/2019 | Mon | Tournament | |
| 5/27/2019 | Mon | Memorial Day | |
| 5/29/2019 | Wed | All Star Manager Vote by Board | |
| 6/3/2019 | Mon | All Star Player Vote by Managers | |
| 6/3-6/7/2019 | | Make Up Games, if needed | |
| 6/6/2019 | Thu | Board Meeting (June) | 5:30pm to 6:30pm |
| Sat | Little League Night at Shorebirds | |
| 6/7/2019 | Fri | PM Rising Stars Game | 6pm to 8:30pm |
| 6/8/2019 | Sat | Tournament | |
| 6/9/2019 | Sun | Tournament | |
| 6/14 - 6/15/2019 | Fri/Sat | PM Tournament @ FLL | |
| 6/22/2019 | Sat | Tournament | |
| 6/23/2019 | Sun | Tournament | |
| 7/6 and 7/7 | | Tournament | |
| 7/11/2019 | Thu | Board Meeting (July) | 5:30pm to 6:30pm |
| 7/13-7/14/2019 | Sat/Sun | Minor & Major Tournament @ FLL | |
| 7/13/2019 | Sat | Fall Ball Online Registration Begins | |
| 7/24/2019 | Wed | Fall Ball Walk-In Registration | 6pm-7:30pm |
| 7/26/2019 | Fri | Tournament | |
| 7/27/2019 | Sat | Tournament | |
| 7/28/2019 | Sun | Tournament | |
| 8/1/2019 | Thu | Board Meeting (Aug) | 5:30pm to 6:30pm |
| 8/7/2019 | Wed | Fall Ball Walk-In Registration | 6pm-7:30pm |
| 8/10/2019 | Sat | Tournament | |
| 8/11/2019 | Sun | Tournament | |
| 8/14/2019 | Wed | Fall Ball Walk-In Registration | 6pm-7:30pm |
| 8/17/2019 | Sat | Fall Ball Walk-In Registration | 10am - 12pm |
| 8/17/2019 | Sat | Finalize Fall Teams and Order Uniforms | |
| 9/2/2019 | Mon | Labor Day | |
| 9/3-9/6/2019 | | Fall Ball Practices | |
| 9/5/2019 | Thu | Board Meeting (Sept) | 5:30pm to 6:30pm |
| 9/9-10/24/2019 | | Fall Ball Games | |
| 10/3/2019 | Thu | Board Meeting (Oct) | 5:30pm to 6:30pm |
| 10/31/2019 | Thu | Halloween | |