| 2019-08-31 15:00:00August 31, 2019 | Kettering 2nd XV vs Oadby Wyggestonians 2nd XV (Pre-Season) | 15:00:003:00 pm | Kettering |
| 2019-09-07 15:00:00September 7, 2019 | Oadby Wyggestonians 2nd XV vs Rugby Lions 2nd XV | 15:00:003:00 pm | Oadby Wyggestonian |
| 2019-09-14 15:00:00September 14, 2019 | Syston 2nd XV vs Oadby Wyggestonians 2nd XV | 13 - 27 | Syston |
| 2019-09-28 15:00:00September 28, 2019 | Oadby Wyggestonians 2nd XV vs Loughborough 2nd XV | 42 - 7 | Oadby Wyggestonian |
| 2019-10-05 15:00:00October 5, 2019 | Kettering 2nd XV vs Oadby Wyggestonians 2nd XV | 24 - 29 | Kettering |
| 2019-10-12 15:00:00October 12, 2019 | Lutterworth 2nd XV vs Oadby Wyggestonians 2nd XV | 19 - 23 | Lutterworth |
| 2019-10-18 15:00:00October 18, 2019 | Stoneygate 2nd XV vs Oadby Wyggestonians 2nd XV | 5 - 31 | Stoneygate |
| 2019-10-26 15:00:02October 26, 2019 | Oadby Wyggestonians 2nd XV vs West Bridgeford 1st XV | 15:00:02Canceled | Oadby Wyggestonian |
| 2019-10-30 19:30:59October 30, 2019 | Syston 2nd XV vs Oadby Wyggestonians 2nd XV | 31 - 17 | Syston |
| 2019-11-09 14:15:00November 9, 2019 | Oadby Wyggestonians 2nd XV vs Leicester Lions 2nd XV | 14:15:002:15 pm | Oadby Wyggestonian |
| 2019-11-16 14:15:00November 16, 2019 | Sutton Bonington Students vs Oadby Wyggestonians 2nd XV | 14:15:00Canceled | Sutton Bonington |
| 2019-11-23 14:15:00November 23, 2019 | Vipers 2nd XV vs Oadby Wyggestonians 2nd XV | 14:15:002:15 pm | Vipers |
| 2019-12-07 14:15:00December 7, 2019 | Oadby Wyggestonians 2nd XV vs Oundle 2nd XV | 14:15:002:15 pm | Oadby Wyggestonian |
| 2019-12-14 14:15:00December 14, 2019 | Peterborough 2nd XV vs Oadby Wyggestonians 2nd XV | 14:15:002:15 pm | Peterborough |
| 2019-12-21 14:15:00December 21, 2019 | Oadby Wyggestonians 2nd XV vs Syston 3rd XV | 14:15:002:15 pm | Oadby Wyggestonian |
| 2020-01-11 14:15:00January 11, 2020 | Rugby Lions 2nd XV vs Oadby Wyggestonians 2nd XV | 14:15:002:15 pm | Rugby Lions |
| 2020-01-18 14:15:00January 18, 2020 | Leicester Lions 2nd XV vs Oadby Wyggestonians 2nd XV | 14:15:002:15 pm | Leicester Lions |
| 2020-01-25 14:15:00January 25, 2020 | Oadby Wyggestonians 2nd XV vs Sutton Bonington Students | 14:15:002:15 pm | Oadby Wyggestonian |
| 2020-02-01 14:15:00February 1, 2020 | Oadby Wyggestonians 2nd XV vs Lutterworth 2nd XV | 14:15:002:15 pm | Oadby Wyggestonian |
| 2020-02-08 14:15:00February 8, 2020 | Oadby Wyggestonians 2nd XV vs Vipers 2nd XV | 14:15:002:15 pm | Oadby Wyggestonian |
| 2020-02-28 14:15:00February 28, 2020 | Oadby Wyggestonians 2nd XV vs Stoneygate 2nd XV | 14:15:002:15 pm | Oadby Wyggestonian |
| 2020-03-07 15:00:00March 7, 2020 | Oadby Wyggestonians 2nd XV vs Kettering 2nd XV | 15:00:003:00 pm | Oadby Wyggestonian |
| 2020-03-21 15:00:00March 21, 2020 | Loughborough 2nd XV vs Oadby Wyggestonians 2nd XV | 15:00:003:00 pm | Loughborough |
| 2020-03-28 15:00:00March 28, 2020 | Oundle 2nd XV vs Oadby Wyggestonians 2nd XV | 15:00:003:00 pm | Oundle |
| 2020-04-04 15:00:00April 4, 2020 | Oadby Wyggestonians 2nd XV vs Peterborough 2nd XV | 15:00:003:00 pm | Oadby Wyggestonian |
