| NEW VISTA OF THE BLUEGRASS INC | Lexington | F32Z Mental Health & Crisis Intervention | $122.1M | 8 |
| SEVEN COUNTIES SERVICES INC | Louisville | F300 Mental Health & Crisis Intervention | $121.6M | 10 |
| Owensboro Health Medical Group Inc | Owensboro | E99 Health Care | $120.4M | 11 |
| NEW VISTA COMMUNITIES INC | Lexington | F33 Mental Health & Crisis Intervention | $113.7M | 8 |
| WEST KENTUCKY RURAL ELECTRIC COOPERATIVE CORPORATION | Mayfield | — | $109.8M | 19 |
| CUMBERLAND FAMILY MEDICAL CENTER INC | Burkesville | E32 Health Care | $109.8M | 18 |
| LIFESKILLS INC | Bowling Green | F80Z Mental Health & Crisis Intervention | $107.9M | 11 |
| FLAGET HEALTH CARE INC | Bardstown | — | $106.8M | 15 |
| HARRISON MEMORIAL HOSPITAL INC | Cynthiana | E22Z Health Care | $102.4M | 9 |
| UNIVERSITY OF LOUISVILLE REAL ESTATE FOUNDATION INC | Louisville | T30 Philanthropy, Voluntarism & Grantmaking Foundations | $100.7M | 1 |
| DISMAS CHARITIES INC | Louisville | P20Z Human Services | $99.7M | 12 |
| JACKSON PURCHASE ENERGY CORPORATION | Paducah | — | $98.1M | 16 |
| KING'S DAUGHTERS MEDICAL SPECIALTIES INC | Ashland | E30 Health Care | $97.4M | 8 |
| HOSPARUS INC HOSPARUS HEALTH | Louisville | P74Z Human Services | $95.6M | 11 |
| NOLIN RURAL ELECTRIC COOPERATIVE CORP | Elizabethtown | — | $94.7M | 13 |
| JANE TODD CRAWFORD MEMORIAL HOSP | Greensburg | E20 Health Care | $94.3M | 0 |
| LEWIS COUNTY PRIMARY CARE CENTER INC | Vanceburg | E32Z Health Care | $94.3M | 6 |
| MOUNTAIN COMPREHENSIVE HEALTH CORPORATION | Whitesburg | E34Z Health Care | $93.7M | 9 |
| Memorial Hospital Inc | Manchester | E220 Health Care | $93.7M | 26 |
| ROCKCASTLE HOSPITAL & RESPIRATORY CARE CENTER INC | Mt Vernon | E22 Health Care | $92.7M | 12 |
| Hospice of the Bluegrass Inc | Lexington | P740 Human Services | $92.7M | 18 |
| GEORGETOWN COLLEGE | Georgetown | B420 Education | $91.9M | 10 |
| THE COMMUNITY FOUNDATION OF LOUISVILLE INC | Louisville | T310 Philanthropy, Voluntarism & Grantmaking Foundations | $90.1M | 8 |
| FLEMING-MASON ENERGY COOPERATIVE INC | Flemingsburg | — | $89.9M | 14 |
| KENTUCKYONE HEALTH MEDICAL GROUP INC | Lexington | E20 Health Care | $86.7M | 17 |
| MEADE COUNTY RURAL ELECTRIC COOPERATIVE CORPORATION | Brandenburg | — | $86.6M | 14 |
| UNIVERSITY OF PIKEVILLE | Pikeville | B420 Education | $86M | 12 |
| LINDSEY WILSON COLLEGE | Columbia | B430 Education | $85.3M | 7 |
| OHIO COUNTY HOSPITAL CORPORATION | Hartford | E22 Health Care | $84.3M | 8 |
| MOUNTAIN PLUS SERVICES INC | Prestonsburg | F19 Mental Health & Crisis Intervention | $81.5M | 9 |
| NEW VISTA BEHAVIORAL HEALTHCARE INC | Lexington | F113 Mental Health & Crisis Intervention | $78.6M | 8 |
| GOD'S PANTRY FOOD BANK INC | Lexington | — | $78.1M | 4 |
| CROSSWATER CANYON INC | Hebron | A50 Arts, Culture & Humanities | $74.3M | 3 |
| Grace Community Health Center Inc | Corbin | E32 Health Care | $73.9M | 9 |
| ANSWERS IN GENESIS INC | Petersburg | X20Z Religion-Related | $73.5M | 9 |
| Owensboro Health Twin Lakes Regional Medical Center Inc | Owensboro | E22 Health Care | $72.1M | 10 |
| TRANSYLVANIA UNIVERSITY | Lexington | B420 Education | $71.8M | 17 |
| COMMUNITY ACTION KENTUCKY INC | Frankfort | S21Z Community Improvement & Capacity Building | $71.4M | 0 |
| INTER-COUNTY ENERGY COOPERATIVE | Danville | — | $71M | 13 |
| CATHOLIC CHARITIES OF LOUISVILLE INC | Louisville | P30Z Human Services | $69.3M | 3 |
| 4 GOOD COMMUNITY INC | Henderson | P20 Human Services | $69.2M | 2 |
| CASEY COUNTY HOSPITAL DISTRICT | Liberty | — | $68.5M | 0 |
| ASBURY COLLEGE | Wilmore | B420 Education | $66.5M | 8 |
| NORTON PROPERTIES INC | Louisville | E110 Health Care | $66M | 7 |
| UNIVERSITY OF LOUISVILLE FOUNDATION INC | Louisville | B110 Education | $65.9M | 3 |
| FARMERS RURAL ELECTRIC COOPERATIVE CORPORATION | Glasgow | — | $65.8M | 14 |
| COUNCIL OF STATE GOVERNMENTS | Lexington | — | $65.4M | 11 |
| Adam R Scripps Foundation | Ft Mitchell | T20 Philanthropy, Voluntarism & Grantmaking Foundations | $63.9M | 1 |
| TAYLOR COUNTY RURAL ELECTRIC COOPERATIVE CORPORATION | Campbellsville | — | $62.8M | 14 |
| NETWORK FOR HOPE INC | Louisville | — | $61.5M | 14 |
