Note, the following motion was passed at the 1997-8 Annual MASSA Meeting: A team that does not participate in a regatta for which they signed up will loose an initial signup round for each missed regatta in the next season's regatta signup session, unless they provide 10 days notice to the district director (or designated alternative) or find another member team to fill in using (1) the list of alternatives as posted on the web site, or (2), if no alternatives can attend, any other member team. At the 2000 Annual Meeting, the director was given the authority to waive the penalty if adequate justification is provided.
| Mar 25 | Apr 1 | Apr 2 | Apr 8 | Apr 9 | Apr 15-16 | Apr 29-30 | Apr 29 | May 7 | May 7 | May 13 |
| Georgetown | Old Dominion University | Ches. Bay Maritime Museum | Severn Sailing Association | Annapolis Yacht Club: extreme conditions, not sailed | Navy Mallory Qualifiers | St Marys Baker Qualifiers | Washington College | U.S. Merchant Marine Academy Championship | USMMA Singlehanded | Stony Brook/ Port Jefferson - not scored yet |
| Annapolis 10 | Southern, MD** | S.Regional NJ 9 | Pt. Pleasant 15 | Southern MD | Pt. Pleasant* | Key School | Southern MD 7 | S. Regional, NJ 26 | Toms River Clay Johnson | Dalton |
| Key School 9 | Severn 11 | Pt Pleasant 8 | S.Regional NJ 14 | Patuxent | Annapolis* | Annapolis | S. Regional, NJ 6 | Key School 24 | Pt. Pleasant Mathew Goetting | St Anns |
| St Marys 8 | Key School 10 | SouthernMD 7 | Irondequoit 13 | Riverhill | Severn* | Stony Brook | Severna Park 5 | Annapolis 22 | Toms River Reed Johnson | Stony Brook |
| SouthernMD7 | Hampton Rds Academy 9 | Gunston 6 | Annapolis 12 | Irondequoit | Stony Brook* | Severn | Loyola 4 | Pt. Pleasant 20 | AACS Nick Van Wagano | St Anthony |
| McQuaid 6 | AACS 8 | Richard Montgomery** | AACS 11 | Pt. Pleasant | Northport | Broadneck | AACS 3 | Irondequoit 18 | AACS Jeremiah Lyons | Schreiber |
| AACS 5 | Broadneck 7 | Talbot County** | Severn 10 | Port Jeff | Southern, MD | Mamaroneck | Patuxent 2 | McQuaid 16 | St Marys | Southhampton |
| Stony Brook 4 | St. Christophers** | St Anselms 3 | McQuaid 9 | Schreiber | McQuaid* | Peninsula Catholic NS | Gunston 1 | Schreiber 14 | Broadneck Warren Richter | 1st alt. Scarsdale |
| Severn 3 | Newport News HS 5 | Severna Park 2 | St Marys 8 | McQuaid | Irondequoit | Northport NS | . | Severn 12 | Patuxent Daniel Schneider | 2nd alt. Port Jeff |
| Severna Park 2 | Penisula Catholic 4 | Stony Brook 1 | Key School 7 | Key School | St Marys | . | . | Stony Brook 10 | Port Jeff James Webster | 3rd alt. Huntington |
| Port Jefferson 1 | Patuxent 3 | Riverhill NS | Stony Brook 6 | Severn | Key School | . | . | St Marys 8 | Port Jeff Alex Grobe | 4th alt. Manhasset |
| . | Norfolk Academy** | . | Southern, MD 5 | Northport NJ | Broadneck | . | . | Mamaroneck 6 | Masters School Nicholas Bergreen | . |
| . | Norfolk Collegiate 1 | . | Broadneck 4 | AACS | S. Regional, NJ* | . | . | Broadneck 4 | Stony Brook Lynn Kubecka | . |
| . | . | Port Jeff 3 | Annapolis | Severna Park | . | . | Patuxent 2 | . | . | |
| . | . | . | Severna Park 2 | Stony Brook | AACS* | . | . | Port Jeff 1 | . | . |
| . | . | . | Riverhill 1 | St Marys | Riverhill | . | . | Southhampton NS | . | . |
| . | . | . | Schreiber NS | Broadneck | Port Jeff NS | . | . | Huntington NS | . | . |
| . | . | . | Northport NS | Severna Park | . | . | . | . | . | |
| . | . | . | . | . | . | . | . | . | . | |
| . | . | . | . | . | . | . | . | 1st alt. | . | . |
| . | . | . | . | . | . | . | . | 2nd alt | . | . |
| . | . | . | . | . | . | . | . | 3nd alt | . | . |
* Prequalified for the Mallory Qualifiers, other entries must qualify by the order of finish at the AYC April 9th regatta, if more than 18 teams want to sail at Navy (which are how many that are signed up as of 9/26/00).
**Unofficial team (non-member, or composite from different schools)
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