| AMERICAN LEGION AUXILIARY 23 WARREN | Bowling Green | — | $5.6M | 0 |
| ARTS OF SOUTHERN KENTUCKY INC | Bowling Green | A61 Arts, Culture & Humanities | $5.5M | 3 |
| KENTUCKY BANKERS ASSOCIATION | Louisville | — | $5.5M | 8 |
| APPALACHIAN FOOTHILLS HOUSING AGENC | Wurtland | L80Z Housing & Shelter | $5.5M | 0 |
| DOE VALLEY ASSOCIATION INC | Brandenburg | — | $5.5M | 2 |
| KENTUCKY ASSOCIATION OF HEALTH PLANS INC | Lexington | — | $5.5M | 1 |
| GOODENOUGH COLLABORATION TRUST | Lexington | T20 Philanthropy, Voluntarism & Grantmaking Foundations | $5.5M | 1 |
| DELTA DENTAL OF KENTUCKY FOUNDATION INC | Louisville | T22 Philanthropy, Voluntarism & Grantmaking Foundations | $5.5M | 1 |
| BRIDGEHAVEN INC | Louisville | F30Z Mental Health & Crisis Intervention | $5.5M | 5 |
| CHRISTIAN BENEVOLENT OUTREACH INC | Lexington | L200 Housing & Shelter | $5.4M | 5 |
| CUMBERLAND TRACE LEGAL SERVICES INC | Bowling Green | I80Z Crime & Legal-Related | $5.4M | 3 |
| CHRYSALIS HOUSE INC | Lexington | F34Z Mental Health & Crisis Intervention | $5.3M | 2 |
| UNIVERSITY OF KENTUCKY ALUMNI ASSOCIATION INC | Lexington | B840 Education | $5.3M | 1 |
| UNITED STATES DRESSAGE FEDERATION | Lexington | — | $5.3M | 1 |
| THE FRATERNITY OF PHI GAMMA DELTA INC | Lexington | — | $5.3M | 3 |
| LEXINGTON HUMANE SOCIETY | Lexington | D200 Animal-Related | $5.3M | 1 |
| PROJECT CAMP INC | Scottsville | E86 Health Care | $5.3M | 2 |
| Honorable Order of Kentucky Colonels Inc | Louisville | S820 Community Improvement & Capacity Building | $5.3M | 2 |
| YOUNG ADULT DEVELOPMENT IN ACTION INC | Louisville | P30 Human Services | $5.3M | 3 |
| 21ST CENTURY PARKS INC | Louisville | N32 Recreation & Sports | $5.3M | 4 |
| CEDAR LAKE FOUNDATION INC | Louisville | P112 Human Services | $5.3M | 4 |
| CATALYTIC DEVELOPMENT FUNDING CORP OF NORTHERN KENTUCKY | Covington | S31 Community Improvement & Capacity Building | $5.2M | 3 |
| COUNTRY CLUB OF PADUCAH INC | Paducah | — | $5.2M | 0 |
| EDGEWOOD ESTATES | Frenchburg | P75Z Human Services | $5.2M | 0 |
| CARE GUIDE PARTNERS INC | Louisville | E92 Health Care | $5.1M | 10 |
| LEXINGTON CEMETERY COMPANY | Lexington | — | $5.1M | 2 |
| KENTUCKY SCHOOL BOARDS ASSOCIATION | Frankfort | — | $5.1M | 3 |
| WEST KENTUCKY ALLIED SERVICES | Mayfield | — | $5.1M | 0 |
| BLUEGRASS CENTER FOR AUTISM INC | Louisville | B28 Education | $5.1M | 1 |
| AMBULANCE INC OF LAUREL COUNTY | London | E62Z Health Care | $5.1M | 4 |
| Appalachian College Association Inc | Lexington | B99Z Education | $5.1M | 2 |
| LOUISVILLE METRO POLICE FOUNDATION INC | Louisville | I01 Crime & Legal-Related | $5.1M | 0 |
| APPALACHIAN RESTORATION PROJECT INC C/O HOPE CITY | Barbourville | F20 Mental Health & Crisis Intervention | $5M | 4 |
| Shawnee Christian Health Center Inc | Louisville | E32 Health Care | $5M | 8 |
| LUTHER F CARSON FOUR RIVERS CENTER INC | Paducah | A61 Arts, Culture & Humanities | $4.9M | 2 |
| BARREN RIVER AREA SAFE SPACE INC | Bowling Green | P43Z Human Services | $4.9M | 0 |
| UNIVERSITY OF KENTUCKY MARKEY CANCER FOUNDATION INC | Lexington | — | $4.8M | 1 |
| KENTUCKY ASSIGNED CLAIMS PLAN | Louisville | — | $4.8M | 1 |
| COMMERCE LEXINGTON INC | Lexington | — | $4.8M | 6 |
| ZOOM GROUP INC | Louisville | — | $4.8M | 1 |
| FELIX E MARTIN JR FOUNDATION INC | Louisville | S11 Community Improvement & Capacity Building | $4.8M | 1 |
| CLINTON AND HICKMAN COUNTY HOSPITAL INC | Clinton | E22Z Health Care | $4.8M | 1 |
| KENTUCKY CATTLEMEN'S ASSOCIATION INC | Lexington | — | $4.8M | 1 |
| RONALD MCDONALD HOUSE CHARITIES OF THE BLUEGRASS INC | Lexington | G30Z Diseases, Disorders & Medical Disciplines | $4.7M | 1 |
| CENTRAL KENTUCKY COMMUNITY FOUNDATION INC | Elizabethtown | B42I Education | $4.7M | 1 |
| LABORERS INTERNATIONAL UNION OF NORTH AMERICA LOCAL 576 | Louisville | — | $4.7M | 3 |
| AUDUBON COUNTRY CLUB | Louisville | — | $4.7M | 4 |
| LINCOLN HERITAGE COUNCIL OF BOY SCOUTS OF AMERICA INC | Louisville | — | $4.7M | 2 |
| Baptist Healthcare Foundation Inc | Louisville | E21I Health Care | $4.7M | 4 |
| APPALSHOP INC | Whitesburg | A200 Arts, Culture & Humanities | $4.7M | 6 |
