| 1 | Winchester Foundation | Unclassified | $5.4M | $4.9M |
| 2 | Community Foundation of Randolph County INC | Philanthropy, Voluntarism & Grantmaking | $4.4M | $17.4M |
| 3 | Randolph County YMCA INC | Unclassified | $1.5M | $3.2M |
| 4 | Randolph County Veterans Shelter INC | Mental Health & Crisis Intervention | $586K | $103K |
| 5 | Winchester Lodge No 1977 Loyal Order of Moose | Unclassified | $516K | $272K |
| 6 | Randolph County Community and Economic Development Foundation | Community Improvement & Capacity Building | $440K | $787K |
| 7 | Fountain Park Cemetery Association | Unclassified | $420K | $411K |
| 8 | Saving the Old Properties INC | Arts, Culture & Humanities | $209K | $24K |
| 9 | Phi Delta Kappa Fraternity | Unclassified | $181K | $1 |
| 10 | Steps INC | Unclassified | $123K | $534K |
| 11 | Trustees of Purdue University | Unclassified | $94K | $0 |
| 12 | Winchester Area Churches & Community Food Pantry | Food, Agriculture & Nutrition | $77K | $205K |
| 13 | Pregnancy Care Center of Randolph | Health Care | $68K | $107K |
| 14 | United Steelworkers | Unclassified | $65K | $82K |
| 15 | Force Band Aides | Arts, Culture & Humanities | $60K | $26K |
| 16 | Winchester Community Athletic Booster Club | Unclassified | $55K | $11K |
| 17 | Indiana Farm Bureau | Unclassified | $51K | $173K |
| 18 | Philip L Huntwork Charitable Trust Agreement | Arts, Culture & Humanities | $1 | $1 |
| 19 | Trustees of Purdue University | Youth Development | $0 | $0 |
| 20 | Trustees of Purdue University | Youth Development | $0 | $0 |
| 21 | Collie Rescue of Indiana | Animal-Related | $0 | $0 |
| 22 | Drug Free Randolph County INC | Mental Health & Crisis Intervention | $0 | $0 |
| 23 | National Council on Youth Leadership | Unclassified | $0 | $0 |
| 24 | Trustees of Purdue University | Youth Development | $0 | $0 |
| 25 | Free & Accepted Masons of Indiana | Unclassified | $0 | $0 |
| 26 | Bear Creek Friends Church | Unclassified | $0 | $0 |
| 27 | Circle X Riders INC | Unclassified | $0 | $0 |
| 28 | Cancer Services for Randolph County INC | Human Services | $0 | $0 |
| 29 | Trustees of Purdue University | Youth Development | $0 | $0 |
| 30 | Trustees of Purdue University | Youth Development | $0 | $0 |
| 31 | Randolph Co Historical Society INC | Unclassified | $0 | $0 |
| 32 | Trustees of Purdue University | Youth Development | $0 | $0 |
| 33 | Trustees of Purdue University | Youth Development | $0 | $0 |
| 34 | Randolph County Invasive Species Exterminators | Environment | $0 | $0 |
| 35 | Randolph County Tourism Commission | Arts, Culture & Humanities | $0 | $0 |
| 36 | Phi Delta Kappa Fraternity | Unclassified | $0 | $0 |
| 37 | Winchester Friends Church | Religion-Related | $0 | $0 |
| 38 | Main Street Christian Church | Unclassified | $0 | $0 |
| 39 | Randolph County Hospital Auxiliary INC | Unclassified | $0 | $0 |
| 40 | Phi Delta Kappa Foundation INC | Unclassified | $0 | $0 |
| 41 | Our Saviour Lutheran Church INC | Unclassified | $0 | $0 |
| 42 | Union St. Wesleyan Church | Unclassified | $0 | $0 |
| 43 | Winchester Church of Christ INC | Unclassified | $0 | $0 |
| 44 | Freedom Life Church | Unclassified | $0 | $0 |
| 45 | Winchester Rotary Foundation INC | Philanthropy, Voluntarism & Grantmaking | $0 | $0 |
| 46 | Voice for Christ Open Bible Church INC | Unclassified | $0 | $0 |
| 47 | Winchester Community Cultural Preservation Committee INC | Recreation & Sports | $0 | $0 |
| 48 | International Association of Fire Fighters | Employment | $0 | $0 |
| 49 | Winchester Downtown Charitable Association INC | Community Improvement & Capacity Building | $0 | $0 |
| 50 | Trustees of Purdue University | Youth Development | $0 | $0 |
| 51 | Trustees of Purdue University | Youth Development | $0 | $0 |
| 52 | Rotary International | Unclassified | $0 | $0 |
| 53 | Kappa Kappa Kappa INC | Unclassified | $0 | $0 |
| 54 | Kiwanis International INC | Community Improvement & Capacity Building | $0 | $0 |
| 55 | Phi Delta Kappa Relief Association | Unclassified | $0 | $0 |
| 56 | Trustees of Purdue University | Youth Development | $0 | $0 |
| 57 | Trustees of Purdue University | Unclassified | $0 | $0 |
| 58 | Randolph County Area Community Theatre INC | Arts, Culture & Humanities | $0 | $0 |
| 59 | New Days Foundation INC | Recreation & Sports | $0 | $0 |
| 60 | Winchester Alumni Association INC | Education | $0 | $0 |
| 61 | Wchs Foorball Club INC | Recreation & Sports | $0 | $0 |
| 62 | Second Chance Foundation INC | Human Services | $0 | $0 |
| 63 | Randolph County Law Enforcement Youth Leadership Camp INC | Youth Development | $0 | $0 |
| 64 | Winchester Alumni Association Scholarship Endowment Fund INC | Education | $0 | $0 |
| 65 | Trustees of Purdue University | Youth Development | $0 | $0 |
| 66 | Randolph County Sharks Swim Team INC | Recreation & Sports | $0 | $0 |
| 67 | Winchester Youth Football Program | Recreation & Sports | $0 | $0 |
| 68 | Falcon Baseball | Recreation & Sports | $0 | $0 |
| 69 | Randolph Amateur Radio Club INC | Arts, Culture & Humanities | $0 | $0 |
| 70 | Winchester Pee Wee Cheer | Recreation & Sports | $0 | $0 |
| 71 | Gracies Gift | Animal-Related | $0 | $0 |
| 72 | Start with Art Ltd | Human Services | $0 | $0 |
| 73 | Winchester Falcon Youth Association INC | Recreation & Sports | $0 | $0 |