First meeting: Sept. 23, 1933 - R.A. Long 26, Woodland 0
Latest meeting: Oct. 10, 2025 - Woodland 41, R.A. Long 0
Next meeting: 2026
Meetings total: 19
All-time series: Woodland Leads 16-3
League series: Woodland Leads 15-3
Post-season series: n/a
Largest victory: Woodland, 60-8 (2006)
Longest win streak: Woodland, 13 (2011-present)
Current win streak: Woodland, 13 (2011-present)
| R.A. Long Victories | Woodland Victories | Tie Games |
| No. | Date | Winning Team | Losing Team | |||
| 1 | Sept. 23, 1933 | at R.A. Long | 26 | Woodland | 0 | |
| 2 | Sept. 29, 2006 | at Woodland* | 60 | R.A. Long | 8 | |
| 3 | Sept. 28, 2007 | Woodland* | 28 | at R.A. Long | 10 | |
| 4 | Oct. 3, 2008 | at Woodland* | 18 | R.A. Long | 12 | |
| 5 | Oct. 2, 2009 | at R.A. Long* | 48 | Woodland | 35 | |
| 6 | Oct. 8, 2010 | at R.A. Long* | 48 | Woodland | 6 | |
| 7 | Oct. 7, 2011 | at Woodland* | 42 | R.A. Long | 14 | |
| 8 | Oct. 16, 2014 | Woodland* | 35 | at R.A. Long | 14 | |
| 9 | Oct. 16, 2015 | at Woodland* | 35 | R.A. Long | 14 | |
| 10 | Sept. 30, 2016 | at Woodland* | 22 | R.A. Long | 8 | |
| 11 | Sept. 29, 2017 | Woodland* | 27 | at R.A. Long | 20 | |
| 12 | Sept. 21, 2018 | at Woodland* | 41 | R.A. Long | 8 | |
| 13 | Sept. 27, 2019 | Woodland* | 55 | at R.A. Long | 7 | |
| 14 | Mar. 5, 2021 | at Woodland* | 35 | R.A. Long | 0 | |
| 15 | Oct. 8, 2021 | Woodland* | 8 | at R.A. Long | 7 | |
| 16 | Oct. 7, 2022 | at Woodland* | 52 | R.A. Long | 21 | |
| 17 | Oct. 6, 2023 | Woodland* | 41 | at R.A. Long | 0 | |
| 18 | Oct. 11, 2024 | at Woodland* | 40 | R.A. Long | 0 | |
| 19 | Oct. 10, 2025 | Woodland* | 41 | at R.A. Long | 0 | |