Cal Ripken Sr. League Awards
The table below lists the Cal Ripken Sr. League Most Outstanding Hitter and Most Outstanding Pitcher for each season since the league's founding in 2005. To view the full awards list for each season (Players of the Week, All-League honors, etc.) click the year on the left side of each row.
| Year | Most Outstanding Player (Hitter) | Most Outstanding Pitcher |
| 2026 | ||
| 2025 | Emilio Gonzalez (Big Train, Florida Atlantic) | Drew Bellis (Big Train, Central Florida) |
| 2024 | Andrew Williamson (Big Train, Central Florida) | Ethan Houghtaling (Aces, Grand Valley State) |
| 2023 | Matt Ossenfort (Aces, Vanderbilt) | Brandon Cassedy (Big Train, Christopher Newport) |
| 2022 | Eddie Hacopian (Aces, Maryland) | Nick Del Prado (Big Train, Florida Atlantic) |
| 2021 | Matt Thomas (Big Train, William & Mary) | Kieran Garner (Thunderbolts, UMBC) |
| 2020 | Season cancelled due to Covid-19 pandemic | |
| 2019 | Kobe Kato (Big Train, Arizona) | Chase Lee (Big Train, Alabama) |
| 2018 | Alec Burleson (Big Train, East Carolina) | William Fleming (Redbirds, Wake Forest) |
| 2017 | James Outman (Big Train, Sacramento State) | Parker Caracci (Redbirds, Ole Miss) |
| 2016 | Vinny Esposito (Big Train, Sacramento State) | Hunter Parsons (Redbirds, Maryland) |
| 2015 | Chris Lewis (Big Train, Sacramento State) | Jack Gomersall (River Dogs, Virginia Military Institute) |
| 2014 | Brandon Lowe (Big Train, Maryland) | Aaron McGarity (Redbirds, Virginia Tech) |
| 2013 | Ian Rice (Redbirds, Chipola) | Bubba Derby (Big Train, San Diego State) |
| 2012 | Hunter Renfroe (Big Train, Mississippi State) | Corey Taylor (Redbirds, UNC Greensboro) |
| 2011 | Adam Barry (Big Train, Cal State Northridge) | Matt Bowman (Big Train, Princeton) |
| 2010 | Benjamin Carhart (Orioles, Stetson) | Max Knowles (Aces, North Carolina Wesleyan) |
| 2009 | Eli Boike (Big Train, Michigan State) |
Jonathan Abramson (Aces, San Francisco) Sander Beck (Orioles, Maryland) |
| 2008 | Mike Celenza (Bombers, Salisbury) | Scott Swinson (Orioles, Lee) |
| 2007 | Eric Allen (Express, Morehead State) | Scott Swinson (Orioles, Lee) |
| 2006 |
Matt Long (Big Train, Santa Clara) Charle Lenhard (Thunderbolts, Akron) |
Hunter Harris (Orioles, Texas) |
| 2005 | Justin McClanahan (Thunderbolts, Louisville) | Bernard Robert (Orioles, Alabama) |