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| Date | Day | Opponent | Place | Time | Score | Box Score |
| Dec 10 | Friday | North Posey | Away | 7:30 p.m. | Heritage Hills 58 North Posey 57 OT | BoxScore |
| Dec 11 | Saturday | Northeast Dubois | Home | 7:00 p.m. | Heritage Hills 82 Northeast Dubois 59 | BoxScore |
| Dec 17 | Friday | Castle | Away | 7:30 p.m. | Castle 71 Heritage Hills 68 | BoxScore |
| Dec 21 | Tuesday | Jasper | Home | 7:00 p.m. | Jasper 44 Heritage Hills 42 | BoxScore |
| Dec 28 | Tuesday | Spencer County Tny | Away | 6:00 p.m. | Heritage Hills 61 Evansville Day 59 | BoxScore |
| Dec 29 | Wednesday | Spencer County Tny | Away | 12:00 p.m. | Heritage Hills 85 Whitesville Trinity 33 | BoxScore |
| Dec 29 | Wednesday | Spencer County Tny | Away | 7:45 p.m. | South Spencer 61 Heritage Hills 48 | BoxScore |
| Jan 7 | Friday | Gibson Southern | Home | 7:30 p.m. | Heritage Hills 62 Gibson Southern 23 | BoxScore |
| Jan 14 | Friday | Pike Central | Home | 7:30 p.m. | Heritage Hills 83 Pike Central 61 | BoxScore |
| Jan 15 | Saturday | Tecumseh | Away | 7:30 p.m. | Heritage Hills 61 Tecumseh 45 | BoxScore |
| Jan 21 | Friday | Southridge | Away | 7:00 p.m. | Southridge 53 Heritage Hills 52 | BoxScore |
| Jan 28 | Friday | Evansville Mater Dei | Away | 7:30 p.m. | Mater Dei 54 Heritage Hills 42 | BoxScore |
| Jan 29 | Saturday | South Spencer | Home | 7:30 p.m. | Heritage Hills 63 South Spencer 56 | BoxScore |
| Feb 1 | Tuesday | Princeton | Away | 7:30 p.m. | Heritage Hills 52 Princeton 47 | BoxScore |
| Feb 4 | Friday | Boonville | Away | 7:30 p.m. | Heritage Hills 44 Boonville 42 | BoxScore |
| Feb 5 | Saturday | Evansville Memorial | Home | 7:30 p.m. | Evansville Memorial 54 Heritage Hills 51 | BoxScore |
| Feb 10 | Thursday | Forest Park | Away | 7:00 p.m. | Forest Park 62 Heritage Hills 57 | BoxScore |
| Feb 12 | Saturday | Tell City | Home | 1:30 p.m. | Heritage Hills 73 Tell City 34 | BoxScore |
| Feb 18 | Friday | Loogootee | Home | 7:00 p.m. | Heritage Hills 72 loogootee 49 | BoxScore |
| Feb 19 | Saturday | Evansville Central | Away | 7:30 p.m. | Evansville Central 88 Heritage Hills 85 OT | BoxScore |
| Feb 25 | Friday | Perry Central | Home | 7:30 p.m. | Perry Central 76 Heritage Hills 71 | BoxScore |
| Mar 1st | tuesday | Mount vernon | Boonville Sectional | 7:30 p.m. | Heritage Hills 57 Mount Vernon 38 | BoxScore |
| Mar 4th | Friday | Boonville | Boonville Sectional | 6:00 p.m. | Boonville 66 Heritage Hills 56 in Double Overtime | BoxScore |