| Sandy Valley Transportation Services Inc | Prestonsburg | — | $8.9M | 1 |
| KENTUCKY ASSOCIATION OF MANUFACTURERS GROUP INSURANCE TRUST | Frankfort | Y43 Mutual & Membership Benefit | $8.8M | 2 |
| FAMILY SCHOLAR HOUSE INC | Louisville | L21 Housing & Shelter | $8.8M | 2 |
| PROTECT OUR SCHOOLS KY | Frankfort | — | $8.7M | 0 |
| BRIDGEMAN CHARITABLE GROUP INC | Louisville | T99 Philanthropy, Voluntarism & Grantmaking Foundations | $8.7M | 0 |
| CATHOLIC EDUCATION FOUNDATION INC | Louisville | B82Z Education | $8.7M | 6 |
| KEY ASSETS KENTUCKY INC | Lexington | F33 Mental Health & Crisis Intervention | $8.7M | 2 |
| BOWLING GREEN - WARREN COUNTY PRIMARY CARE CENTER INC | Bowling Green | B99 Education | $8.6M | 9 |
| HOME FOR THE AGED OF THE LITTLE SISTERS OF THE POOR INC | Louisville | P750 Human Services | $8.6M | 1 |
| FORT CAMPBELL HISTORICAL FOUNDATION | Ft Campbell | C99Z Environment | $8.5M | 1 |
| IPA Crewmember VEBA Trust | Louisville | Y43 Mutual & Membership Benefit | $8.5M | 0 |
| LOUISVILLE COUNTRY CLUB | Louisville | — | $8.4M | 6 |
| SOCIETY OF ST VINCENT DE PAUL COUNCIL OF LOUISVILLE INC | Louisville | L21 Housing & Shelter | $8.4M | 3 |
| FOUNDATION FOR APPALACHIAN KENTUCKY INC | Hazard | T31 Philanthropy, Voluntarism & Grantmaking Foundations | $8.4M | 1 |
| REDBANKS COLONIAL TERRACE INC | Sebree | E91 Health Care | $8.3M | 6 |
| PRICHARD COMMITTEE FOR ACADEMIC EXCELLENCE INC | Lexington | B24E Education | $8.3M | 5 |
| DIOCESAN CATHOLIC CHILDREN'S HOME INC | Ft Mitchell | — | $8.3M | 2 |
| KENTUCKY PHARMACY EDUCATION & RESEARCH FOUNDATION INC | Frankfort | — | $8.3M | 1 |
| ASMARK INSTITUTE INC | Owensboro | K01 Food, Agriculture & Nutrition | $8.3M | 7 |
| KENTUCKY DERBY FESTIVAL INC | Louisville | — | $8.3M | 5 |
| RITA JUNE FOUNDATION INC | Louisville | P20 Human Services | $8.2M | 0 |
| USPIRITUS INC (BELLEWOOD & BROOKLAWN) | Louisville | F01 Mental Health & Crisis Intervention | $8.2M | 1 |
| EQUESTRIAN EVENTS INC | Lexington | — | $8.2M | 3 |
| CARMELITE SISTERS OF THE DIVINE HEART OF JESUS OF KENTUCKY | Owensboro | — | $8.1M | 0 |
| LICKING VALLEY COMMUNITY ACTION PROGRAM | Flemingsburg | P20Z Human Services | $8.1M | 1 |
| DISMAS CHARITIES PROPERTIES INC | Louisville | — | $8.1M | 11 |
| PORTLAND CHRISTIAN SCHOOL SYSTEM INC | Louisville | B20 Education | $8.1M | 4 |
| KENTUCKY NATURAL LANDS TRUST INC | Berea | C360 Environment | $8.1M | 1 |
| LESLIE KNOTT LETCHER PERRY HEADSTART INC | Hazard | B22Z Education | $8.1M | 1 |
| EXPREE CREDIT UNION | Frankfort | — | $8M | 3 |
| FOOTHILLS ACADEMY INC | Albany | I21 Crime & Legal-Related | $8M | 2 |
| CEDAR LAKE RESIDENCES INC | Louisville | L80Z Housing & Shelter | $8M | 4 |
| ACCESS VENTURES INC | Louisville | S12 Community Improvement & Capacity Building | $8M | 1 |
| IDLE HOUR COUNTRY CLUB | Lexington | N50 Recreation & Sports | $7.9M | 3 |
| CONNECTED NATION INC | Bowling Green | B99 Education | $7.9M | 7 |
| Beyond Blue Corporation | Lexington | B05 Education | $7.9M | 8 |
| PINEVILLE COMMUNITY HEALTH CENTER INC | Pineville | E22 Health Care | $7.9M | 2 |
| HOSPICE CARE PLUS INC | Richmond | P74 Human Services | $7.8M | 2 |
| Pentescostal Childrens Home Inc | Barbourville | — | $7.8M | 0 |
| NATIONAL SOCIETY OF THE SONS OF THE AMERICAN REVOLUTION | Louisville | A800 Arts, Culture & Humanities | $7.8M | 4 |
| AMERICAN ASSOCIATION OF EQUINE PRACTITIONERS | Lexington | — | $7.8M | 5 |
| RUSSELL DEVELOPMENT COMPANY INC | Louisville | T30 Philanthropy, Voluntarism & Grantmaking Foundations | $7.7M | 0 |
| THE POINT PROGRAMS INC | Covington | J22Z Employment | $7.7M | 0 |
| MASTER PROVISIONS INC | Florence | Z99Z Unknown | $7.7M | 1 |
| KENTUCKY BAR ASSOCIATION | Frankfort | — | $7.7M | 1 |
| PLUMBERS 452 HEALTH & WELFARE FUND | Lexington | — | $7.7M | 0 |
| BAWAC INC | Florence | J200 Employment | $7.7M | 3 |
| PENNYROYAL HEALTH CARE SERVICES | Princeton | E32 Health Care | $7.7M | 0 |
| SHAKERTOWN AT PLEASANT HILL KENTUCKY INC | Harrodsburg | A540 Arts, Culture & Humanities | $7.6M | 6 |
| FATHER MALONEY'S BOY'S HAVEN INC | Louisville | P70Z Human Services | $7.6M | 2 |
