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| – | Team | Rank | VS | Rank | Opp Team | Details |
| 1 | Calvert Hall | #3 | vs | #1 | McDonogh | 03/27/2020 |
| 2 | Gilman | #4 | vs | #1 | McDonogh | 05/05/2020 |
| 3 | Calvert Hall | #3 | vs | #4 | Gilman | 04/17/2020 |
| 4 | Georgetown Prep | #2 | vs | #7 | Haverford School | 03/21/2020 |
| 5 | Boys Latin | #10 | vs | #1 | McDonogh | 05/02/2020 |
| 6 | Georgetown Prep | #2 | vs | #9 | St Stephen-St Agnes | 04/24/2020 |
| 7 | Boys Latin | #10 | vs | #3 | Calvert Hall | 04/28/2020 |
| 8 | Boys Latin | #10 | vs | #4 | Gilman | 04/14/2020 |
| 9 | McDonogh | #1 | vs | #13 | St Pauls MD | 03/31/2020 |
| 10 | Dallas Jesuit | #5 | vs | #9 | St Stephen-St Agnes | 03/28/2020 |
| 11 | McDonogh | #1 | vs | #14 | Ponte Vedra | 03/16/2020 |
| 12 | Dallas Jesuit | #5 | vs | #11 | Highland Park TX | 04/24/2020 |
| 13 | Calvert Hall | #3 | vs | #13 | St Pauls MD | 04/07/2020 |
| 14 | Culver Military Academy Prep | #15 | vs | #1 | McDonogh | 03/23/2020 |
| 15 | Gilman | #4 | vs | #13 | St Pauls MD | 03/27/2020 |
| 16 | Loyola-Blakefield | #17 | vs | #1 | McDonogh | 04/03/2020 |
| 17 | Calvert Hall | #3 | vs | #17 | Loyola-Blakefield | 05/05/2020 |
| 18 | Highland Park TX | #11 | vs | #9 | St Stephen-St Agnes | 03/25/2020 |
| 19 | Gilman | #4 | vs | #17 | Loyola-Blakefield | 05/01/2020 |
| 20 | Georgetown Prep | #2 | vs | #19 | St Christophers | 03/31/2020 |
| 21 | Culver Military Academy Prep | #15 | vs | #6 | Gonzaga | 03/27/2020 |
| 22 | Culver Military Academy Prep | #15 | vs | #7 | Haverford School | 03/25/2020 |
| 23 | Gilman | #4 | vs | #18 | Jupiter | 03/18/2020 |
| 24 | Boys Latin | #10 | vs | #13 | St Pauls MD | 05/05/2020 |
| 25 | Bullis | #21 | vs | #2 | Georgetown Prep | 04/28/2020 |