All Challenger Division games are played 1:30 to 3:30 p.m. on Sundays at Friendship Field #3. Each week Challenger players are teamed with players from the Majors Division.
For spring 2009, Challenger Division games will start on April and go through the first weekend in June. The official game schedule will be finalized in late March.
| Challenger Season | |
| Sunday, April 19 | |
| Majors Team | Time |
| All | 1:30 |
| Sunday, April 26 | |
| Majors Team | Time |
| Red Sox | 1:30 |
| Sunday, May 3 | |
| Majors Team | Time |
| Dodgers | 1:30 |
| Sunday, May 10 | |
| Majors Team | Time |
| Reds | 1:30 |
| Sunday, May 17 | |
| Majors Team | Time |
| Rays | 1:30 |
| Sunday, May 31 | |
| Majors Team | Time |
| Tigers | 1:30 |
| Sunday, June 7 | |
| Majors Team | Time |
| As and Yankees | 1:30 |