| JEFFERSON COUNTY HISTORICAL SOCIETY | IN | 7 | 2024 | $316,070 |
| FIRST CHRISTIAN CHURCH | IN | 7 | 2024 | $280,620 |
| GIRLS INCORPORATED OF JEFFERSON COUNTY INDIANA | IN | 7 | 2024 | $208,200 |
| PRINCE OF PEACE CATHOLIC CHURCH | IN | 7 | 2024 | $160,600 |
| FRIENDS OF THE OHIO THEATRE | IN | 4 | 2024 | $142,324 |
| MADISON-JEFFERSON COUNTY HUMANE SOCIETY INC | IN | 7 | 2024 | $98,000 |
| JEFFERSON COUNTY HOUSE OF HOPE INC | IN | 6 | 2024 | $83,885 |
| SPRINGDALE CEMETERY ASSOCIATION | IN | 4 | 2024 | $66,942 |
| HISTORIC MADISON INC | IN | 3 | 2024 | $66,000 |
| MADISON CONSOLIDATED SCHOOLS EDUCATIONAL FOUNDATION INC | IN | 6 | 2024 | $61,150 |
| HISTORIC HOOSIER HILLS R C & D INC | IN | 7 | 2024 | $58,200 |
| MADISON RIVERFRONT DEVELOPMENT CORPORATION | IN | 3 | 2024 | $56,700 |
| JEFFERSON COUNTY YOUTH SHELTER INC | IN | 7 | 2024 | $55,250 |
| RIVER VALLEY RESCOURCES INC | IN | 3 | 2024 | $39,489 |
| MADISON AREA ARTS ALLIANCE INC | IN | 3 | 2024 | $38,500 |
| FRIENDS OF CLIFTY FALLS STATE PARK | IN | 2 | 2024 | $37,850 |
| JEFFERSON COUNTY PRESERVATION COUNCIL INC | IN | 2 | 2024 | $27,000 |
| LIFETIME RESOURCES INC | IN | 2 | 2024 | $25,543 |
| SAFE PASSAGE INC | IN | 3 | 2024 | $22,242 |
| JEFFERSON COUNTY VETERANS COUNCIL | IN | 2 | 2024 | $17,368 |
| FREEDOM CENTER INC | IN | 2 | 2024 | $15,500 |
| BIG BROTHERS BIG SISTERS OF SOUTHEAST INDIANA INC | IN | 1 | 2024 | $7,214 |
| HERITAGE TRAIL CONSERVANCY INC | IN | 4 | 2023 | $66,300 |
| KINDNESS JEFFERSON COUNTY INDIANA INC | IN | 1 | 2023 | $22,500 |
| HABITAT FOR HUMANITY INTERNATIONAL INC | IN | 2 | 2023 | $16,000 |
| MADISON MAIN STREET PROGRAM INC | IN | 1 | 2023 | $11,500 |
| FRIENDS OF CAMP LOUIS ERNST INC | IN | 1 | 2023 | $5,400 |
| LIDE WHITE MEMORIAL BOYS AND GIRLS CLUB INC | IN | 5 | 2022 | $141,900 |
| CHILDRENS ADVOCACY CENTER OF SOUTHEASTERN INDIANA INCORPORATED | IN | 2 | 2022 | $47,190 |
| JEFFERSON COUNTY UNITED WAY INC | IN | 3 | 2022 | $20,600 |
| INDIAN-KENTUCK BAPTIST CHURCH | IN | 1 | 2022 | $20,000 |
| FRIENDS OF THE JEFFERSON COUNTY ANIMAL SHELTER INC | IN | 1 | 2022 | $15,300 |
| HANOVER COMMUNITY GARDEN INC | IN | 1 | 2022 | $10,000 |
| WE BLOOM INC | IN | 1 | 2022 | $5,650 |
| OHIO VALLEY OPPORTUNITIES INC | IN | 3 | 2021 | $28,537 |
| MADISON MUSIC MOVEMENT INC | IN | 2 | 2021 | $18,900 |
| HISTORIC ELEUTHERIAN COLLEGE INC | IN | 1 | 2021 | $10,000 |
| DEVELOPMENTAL SERVICES INC | IN | 1 | 2021 | $6,549 |
| MADISON PERFORMING ARTS FOUNDATION INC | IN | 1 | 2021 | $6,200 |
| SOUTHWESTERN POOL BOOSTERS INC | IN | 1 | 2020 | $7,175 |
| FRIENDS OF CANAAN INC | IN | 1 | 2020 | $7,049 |
| DEPUTY VOLUNTEER FIRE COMPANY INC | IN | 1 | 2019 | $38,000 |
| MADISON YOUTH UNLIMITED INC | IN | 1 | 2019 | $24,800 |
| BOY SCOUTS OF AMERICA | IN | 1 | 2019 | $10,000 |
| HOOSIERS FEEDING THE HUNGRY INC | IN | 1 | 2019 | $10,000 |
| JEFFERSON COUNTY TRANSITIONAL SERVICES INC | IN | 1 | 2018 | $10,525 |
| CENTERSTONE HEALTH SERVICES INC | IN | 1 | 2018 | $5,500 |
| KENT VOLUNTEER FIRE COMPANY | IN | 1 | 2018 | $5,200 |