* Conference Event
% Exhibition/Scrimmage Event
Event times are (CST)
| December |
| * | 4 | 7:45PM | Plainville High School | @ | Osborne | 73-38 | |
| | Pville: Perkins 32. led 28-27 at half. 28-3 3rd qtr. Osborne: DeMars 13, Bertrand 11 | |
| | 10 | 5:30PM | Thunder Ridge | vs. | Osborne | 53-39 | |
| | Lakeside Preseason Tournament: TR: Yoxall 14, Rietzke 11, Horn 10. Osborne: Bertrand 15, DeMars 13. | |
| | 11 | 8:30PM | Osborne | @ | Lakeside | 37-45 | |
| | Lakeside Preseason Tournament: Lside: Heiland 16, Shoemaker 11. Osborne: Mick 12. | |
| | 12 | 3:30PM | Tipton | vs. | Osborne | 50-46 | |
| | Lakeside Preseason Tournament: Tipton: Grief 14, Hollerich 12. Osborne: Mick 16, Bertrand 14. | |
| * | 18 | 7:45PM | Ellis High School | @ | Osborne | 59-22 | |
| | Osborne: Mick 11 | |
| January |
| | 5 | 7:45PM | Beloit | @ | Osborne | 60-43 | |
| | Beloit: Catlin 17, Brummer 16. Osborne: Demars 10. | |
| * | 8 | 7:45PM | Osborne | @ | Norton High School | 29-64 | |
| | Osborne: Trailed 44-15 at half. Mick 12. | |
| | 11 | 7:45PM | Lincoln | @ | Osborne | 50-53 | |
| | Osb: led 32-19 half. DeMars 26, Mick 14. Lincoln: Farris 17, Schroeder 14, Aufdemberge 10. | |
| * | 12 | 7:45PM | Phillipsburg High School | @ | Osborne | 54-41 | |
| | Osborne: Mick 15. | |
| | 16 | 7:30PM | Osborne | vs. | Phillipsburg High School | 36-45 | |
| | MCL Tournament-Feather Bracket @ Plainville. Osborne: Bertrand 13. | |
| | 26 | 7:45PM | Lakeside | @ | Osborne | 50-44 | |
| | Lake: Heiland & Shoemaker 17. Osborne: DeMars 10. | |
| * | 29 | 7:45PM | Osborne | @ | Stockton High School | 40-57 | |
| | Osborne: Down 18-7 1st qtr. Mick 14, Schurr 10. | |
| February |
| * | 5 | 7:45PM | Trego Community High School | @ | Osborne | 39-31 | |
| | 9 | 7:45PM | Smith Center | @ | Osborne | 53-42 | |
| | SC: Corbett 22, Terrill 11. Osborne: Mick 17. | |
| | 12 | 7:45PM | Osborne | @ | Phillipsburg High School | 41-54 | |
| | Osborne: Mick 16. | |
| | 16 | 7:30PM | Osborne | @ | Sylvan-Lucas | 35-42 | |
| | SU: Workman 20. Osborne: Mick 11. | |
| * | 19 | 7:45PM | Hill City High School | @ | Osborne | 55-37 | |
| | Osborne: Mick 13, Bertrand 11, Schurr 10. | |
| | 23 | 7:45PM | Rock Hills | @ | Osborne | 49-47 | |
| | RH: Ost 22, Konen 15. Osborne: Mick 15, Schurr 13. | |
| * | 25 | 7:45PM | Osborne | @ | Smith Center | 40-58 | |
| | SC: 18-4 1st Q. Corbett 23, 14 reb, Hobelmann 11. Osborne: Slothower 12, Mick 11. | |
| March |
| | 2 | 7:00PM | Osborne | @ | Sacred Heart | 26-61 | |
| | 2A Sub-State 1st Rd.: SH: Toogood 12, Windholz 10. | |
* Conference Event
% Exhibition/Scrimmage Event
Event times are (CST)
