| Sat | 8/24/2019 2:00:00 PM | Varsity Football @ Lynnfield (Scrimmage) | Lynnfield H.S. |
| Sun | 8/24/2019 4:00:00 PM | Concert: Mule Foot | Topsfield Common |
| Sat | 8/24/2019 5:00:00 PM | JV Boys Soccer v Andover (scrimmage) | Masco Soccer Field |
| Sat | 8/24/2019 5:00:00 PM | Varsity Boys Soccer v Andover (scrimmage) | Masco Soccer Field |
| Sun | 8/25/2019 6:00:00 PM | Concert: Oberlander Hofbrau Band | North Andover Town Common |
| Mon - TO BE RESCHEDULED | 8/26/2019 6:00:00 PM | FINALS - Chiefs VS. WINNER GAME 17 (BEST OF 3) | TBD |
| Tue - TO BE RESCHEDULED | 8/27/2019 6:00:00 PM | FINALS - Chiefs VS. WINNER GAME 17 (BEST OF 3) | TBD |
| Tue | 8/27/2019 7:30:00 PM | Concert: M ood Swings Big Band | 17 Union St, Ipswich |
| Wed | 8/28/2019 4:00:00 PM | JV Boys Soccer v Central Catholic (scrimmage) | Masco Soccer Field |
| Wed | 8/28/2019 4:00:00 PM | JV2 Boys Soccer v Central Catholic | Masco Soccer Field |
| Wed | 8/28/2019 4:00:00 PM | Varsity Boys Soccer v Central Catholic (scrimmage) | Masco Soccer Field |
| Wed - TO BE RESCHEDULED | 8/28/2019 6:00:00 PM | FINALS - Chiefs VS. WINNER GAME 17 (BEST OF 3) | TBD |
| Thu | 8/29/2019 6:30:00 PM | Concert: Way Up South | 381 Main St, West Newbury |
| Sat - time TBD | 9/1/2019 1:23:00 AM | JV Girls Soccer v Marshfield | Masco Soccer Field |
| Tue | 9/3/2019 4:00:00 PM | JV Boys Soccer @ St John's Prep | St. John's Prep |
| Tue | 9/3/2019 4:00:00 PM | JV Volleyball v North Andover | Masco Gym |
| Tue | 9/3/2019 4:00:00 PM | Varsity Boys Soccer @ St John's Prep | St. John's Prep |
| Tue | 9/3/2019 5:30:00 PM | Varsity Volleyball v North Andover | Masco Gym |
| Wed | 9/4/2019 3:45:00 PM | JV Boys Soccer v Lynnfield | Masco Soccer Field |
| Wed | 9/4/2019 3:45:00 PM | JV Girls Soccer @ Lynnfield | Lynnfield H.S. |
| Wed | 9/4/2019 3:45:00 PM | Varsity Boys Soccer v Lynnfield | Masco Soccer Field |
| Thu | 9/4/2019 3:45:00 PM | Varsity Girls Hockey v Lynnfield | Masco Field Hockey Field |
| Wed | 9/4/2019 3:45:00 PM | Varsity Girls Soccer @ Lynnfield | Lynnfield H.S. |
| Wed | 9/4/2019 4:00:00 PM | JV Volleyball @ Pentucket | Pentucket H.S. |
| Wed | 9/4/2019 5:30:00 PM | Varsity Volleyball @ Pentucket | Pentucket H.S. |
| Thu | 9/5/2019 5:15:00 PM | JV Girls Hockey v Lynnfield | Masco Field Hockey Field |
| Thu | 9/5/2019 7:00:00 PM | Topsfield School Committee | Proctor School Library, Topsfield |
| Fri | 9/6/2019 3:45:00 PM | JV Boys Soccer v Newburyport | Masco Soccer Field |
| Fri | 9/6/2019 3:45:00 PM | JV Girls Soccer @ Newburyport | Newburyport H.S. |
| Fri | 9/6/2019 3:45:00 PM | Varsity Boys Soccer v Newburyport | Masco Soccer Field |
| Fri | 9/6/2019 3:45:00 PM | Varsity Girls Soccer @ Newburyport | Newburyport H.S. |
| Fri | 9/6/2019 4:00:00 PM | JV Volleyball v Georgetown | Masco Gym |
| Fri | 9/6/2019 5:30:00 PM | Varsity Volleyball v Georgetown | Masco Gym |
| Fri | 9/6/2019 7:00:00 PM | Varsity Football v Danvers | Masco Football Field |
| Sat | 9/7/2019 9:00:00 AM | BAA Soccer Boys Gr4 Bearcats v Methuen Cobras | Chadwick #10 |
| Sat | 9/7/2019 9:00:00 AM | TAA Soccer Boys Gr6 Masco Sounders v Salem Hurricanes | Klock #2 |
| Sat | 9/7/2019 9:00:00 AM | TAA Soccer Boys Gr8 Masco Arsenal v Newburyport FC Ajax | Boxford Common #3 |
| Sat | 9/7/2019 9:00:00 AM | TAA Soccer Girls Gr6 Masco Stars v Andover Mystique | Boy Scout #1 |
| Sat | 9/7/2019 10:30:00 AM | BAA Soccer Girls Gr4 Strikers v Lynn Fireflies | Chadwick #10 |
| Sat | 9/7/2019 10:30:00 AM | TAA Soccer Boys Gr4 Revolution v Georgetown Red Star | Klock #1 |
| Sat | 9/7/2019 10:30:00 AM | TAA Soccer Boys Gr8 Masco Hot Spurs v Andover Red Devils | Boxford Common #3 |
| Sat | 9/7/2019 10:30:00 AM | TAA Soccer Girls Gr6 Masco Bolts v Pentucket Pride | Boy Scout #1 |
| Sat | 9/7/2019 12:00:00 PM | BAA Soccer Girls Gr4 Stars v Wakefield Royals | Chadwick #10 |
| Sat | 9/7/2019 12:00:00 PM | TAA Soccer Boys Gr4 United v Wakefield Barcelona | Klock #1 |
| Sat | 9/7/2019 12:00:00 PM | TAA Soccer Girls Gr6 Masco Comets v Manchester-Essex Nor'Easters | Boy Scout #1 |
| Sat | 9/7/2019 1:30:00 PM | BAA Soccer Girls Gr4 Galaxy v Triton Strikers | Chadwick #10 |
| Sat | 9/7/2019 1:30:00 PM | TAA Soccer Boys Gr4 Galaxy v Ham-Wen Cosmos | Klock #1 |
| Sat | 9/7/2019 1:30:00 PM | TAA Soccer Girls Gr6 Masco Force v Danvers Courage | Boy Scout #1 |
| Sat | 9/7/2019 1:30:00 PM | TAA Soccer Girls Gr8 Masco Breakers v Andover Cobras | Chadwick #11 |
| Sat | 9/7/2019 3:00:00 PM | TAA Soccer Girls Gr4 Breakers v Marblehead Osprey | Klock #1 |
| Sat | 9/7/2019 3:00:00 PM | TAA Soccer Girls Gr6 Masco Meteors v Beverly Mountain Lions | Boy Scout #1 |
| Sat | 9/7/2019 3:00:00 PM | TAA Soccer Girls Gr8 Masco Fire v Peabody United | Chadwick #11 |
| Sat | 9/8/2019 10:00:00 AM | Beverly Regional Airshow | Beverly Airport |