| Day | Date | From | To | Type | Location | Opponent / Sharing With |
|---|---|---|---|---|---|---|
| Tuesday | August 27, 2019 | 5:30 PM | 6:20 PM | Practice | Essex Rink 1 | Peewee 2 |
| Tuesday | August 27, 2019 | 6:35 PM | 7:00 PM | Meeting | Essex Sports Center | |
| Thursday | August 29, 2019 | 5:30 PM | 6:20 PM | Practice | Essex Rink 1 | Peewee 2 |
| Wednesday | September 4, 2019 | 7:30 PM | 8:30 PM | Practice | Mass Bay | |
| Thursday | September 5, 2019 | 5:30 PM | 6:20 PM | Practice | Essex Rink 1 | Peewee 2 |
| Sunday | September 8, 2019 | 8:10 AM | 9:10 AM | Game | Fessenden | vs. Medfield Peewee - "AA" |
| Tuesday | September 10, 2019 | 6:30 PM | 7:20 PM | Practice | Essex Rink 1 | Peewee 2 |
| Thursday | September 12, 2019 | 6:30 PM | 7:20 PM | Practice | Essex Rink 1 | Peewee 2, Bantam 1, Bantam 2, Lady Chieftain U12 WHITE |
| Friday | September 13, 2019 | 7:30 PM | 8:20 PM | Practice | Essex Rink 1 | Peewee 2 |
| Sunday | September 15, 2019 | 6:50 PM | 7:50 PM | Game | Hockeytown 4 | vs. Andover Peewee - "AA1" |
| Tuesday | September 17, 2019 | 6:30 PM | 7:20 PM | Practice | Essex Rink 1 | Peewee 2 |
| Thursday | September 19, 2019 | 6:30 PM | 7:20 PM | Practice | Essex Rink 1 | Bantam 1, Bantam 2, LC Skills PB, Peewee 2 |
| Thursday | September 19, 2019 | 8:05 PM | 9:05 PM | Game | Haverhill - Blue | vs. Wilmington Peewee - "AA" |
| Friday | September 20, 2019 | 7:30 PM | 8:20 PM | Practice | Essex Rink 1 | Peewee 2 |
| Sunday | September 22, 2019 | 2:40 PM | 3:40 PM | Game | Hockeytown 3 | vs. No Andover Peewee - "AA" |
| Tuesday | September 24, 2019 | 6:30 PM | 7:20 PM | Practice | Essex Rink 1 | Peewee 2 |
| Thursday | September 26, 2019 | 6:30 PM | 7:20 PM | Practice | Essex Rink 1 | Bantam 1, Bantam 2, Lady Chieftain U12 RED, Peewee 2 |
| Friday | September 27, 2019 | 7:30 PM | 8:20 PM | Practice | Essex Rink 1 | Peewee 2 |
| Saturday | September 28, 2019 | 3:10 PM | 4:10 PM | Game | Lawrence | vs. Rochester Peewee - "AA" |
| Sunday | September 29, 2019 | 4:45 PM | 5:45 PM | Game | Haverhill - Gold | vs. Haverhill Peewee - "AA" |
| Tuesday | October 1, 2019 | 6:30 PM | 7:20 PM | Practice | Essex Rink 1 | Peewee 2 |
| Thursday | October 3, 2019 | 6:30 PM | 7:20 PM | Practice | Essex Rink 1 | Peewee 2, Bantam 1, Bantam 2, Lady Chieftain U12 RED |
| Friday | October 4, 2019 | 7:30 PM | 8:20 PM | Practice | Essex Rink 1 | Peewee 2 |
| Monday | October 7, 2019 | 8:15 PM | 9:15 PM | Game | Haverhill - Gold | vs. Wilmington Peewee - "AA" |
| Tuesday | October 8, 2019 | 6:30 PM | 7:20 PM | Practice | Essex Rink 1 | Peewee 2 |
| Thursday | October 10, 2019 | 6:30 PM | 7:20 PM | Practice | Essex Rink 1 | Peewee 2, Bantam 1, Bantam 2, Lady Chieftain U12 RED |
| Friday | October 11, 2019 | 7:30 PM | 8:20 PM | Practice | Essex Rink 1 | Peewee 2 |
| Tuesday | October 15, 2019 | 6:30 PM | 7:20 PM | Practice | Essex Rink 1 | Peewee 2 |
| Thursday | October 17, 2019 | 6:30 PM | 7:20 PM | Practice | Essex Rink 1 | Peewee Skills, Peewee 2, Bantam 1, Bantam 2, Lady Chieftain U12 RED |
| Friday | October 18, 2019 | 7:30 PM | 8:20 PM | Practice | Essex Rink 1 | Peewee 2 |
| Saturday | October 19, 2019 | 6:30 AM | 7:30 AM | Game | Haverhill - Blue | vs. Andover Peewee - "AA1" |
| Tuesday | October 22, 2019 | 6:30 PM | 7:20 PM | Practice | Essex Rink 1 | Peewee 2 |
| Thursday | October 24, 2019 | 6:30 PM | 7:20 PM | Practice | Essex Rink 1 | Peewee 2, Bantam 1, Bantam 2, Lady Chieftain U12 RED |
| Thursday | October 24, 2019 | 7:00 PM | 8:00 PM | Game | Haverhill - Blue | vs. No Andover Peewee - "AA" |
| Friday | October 25, 2019 | 6:00 PM | 7:00 PM | Game | Malden | vs. Woburn Peewee - "AA" |
| Friday | October 25, 2019 | 7:30 PM | 8:20 PM | Practice | Essex Rink 1 | Peewee 2 |
| Saturday | October 26, 2019 | 4:50 PM | 5:50 PM | Game | Haverhill - Gold | vs. Rochester Peewee - "AA" |
| Tuesday | October 29, 2019 | 6:30 PM | 7:20 PM | Practice | Essex Rink 1 | Peewee 2 |
| Thursday | October 31, 2019 | 4:00 PM | 5:00 PM | Other | 1980 Rink | |
| Thursday | October 31, 2019 | 5:10 PM | 6:10 PM | Other | 1980 Rink | |
| Thursday | October 31, 2019 | 6:30 PM | 7:20 PM | Practice | Essex Rink 1 | Bantam 1, Bantam 2, Peewee 2, Lady Chieftain U12 RED |
| Thursday | October 31, 2019 | 6:50 PM | 7:50 PM | Game | USA Rink | vs. Central Mass Outlaws |
| Friday | November 1, 2019 | 11:30 AM | 12:30 PM | Game | Saranac Rink | vs. CT Jr Whalers |
| Friday | November 1, 2019 | 4:10 PM | 5:10 PM | Other | '32 Rink | |
| Friday | November 1, 2019 | 6:30 PM | 7:30 PM | Game | 1980 Rink | vs. New Canaan Winter Club |
| Saturday | November 2, 2019 | 12:40 PM | 1:40 PM | Game | USA Rink | vs. Rochester Blackhawks |
| Tuesday | November 5, 2019 | 6:30 PM | 7:20 PM | Practice | Essex Rink 1 | Peewee 2 |
| Thursday | November 7, 2019 | 6:30 PM | 7:20 PM | Practice | Essex Rink 1 | Bantam 1, Bantam 2, Peewee 2, Lady Chieftain U12 RED |
| Friday | November 8, 2019 | 7:20 PM | 8:20 PM | Game | Haverhill - Gold | vs. Warriors U12 - T1 |
| Friday | November 8, 2019 | 7:30 PM | 8:20 PM | Practice | Essex Rink 1 | Peewee 2 |
| Sunday | November 10, 2019 | 1:30 PM | 2:30 PM | Game | North Star C | vs. Demons Peewee - "AA1" |
| Tuesday | November 12, 2019 | 6:30 PM | 7:20 PM | Practice | Essex Rink 1 | Peewee 2 |
| Thursday | November 14, 2019 | 6:30 PM | 7:20 PM | Practice | Essex Rink 1 | Bantam 1, Bantam 2, Peewee 2, Lady Chieftain U12 RED |
| Friday | November 15, 2019 | 7:30 PM | 8:20 PM | Practice | Mass Bay | |
| Saturday | November 16, 2019 | 4:20 PM | 5:20 PM | Game | Lawrence | vs. Rochester Peewee - "AA" |
| Tuesday | November 19, 2019 | 6:30 PM | 7:20 PM | Practice | Essex Rink 1 | Peewee 2 |
| Thursday | November 21, 2019 | 6:30 PM | 7:20 PM | Practice | Essex Rink 1 | Bantam 1, Bantam 2, Peewee 2, Lady Chieftain U12 RED |
| Thursday | November 21, 2019 | 8:05 PM | 9:05 PM | Game | Haverhill - Blue | vs. No Andover Peewee - "AA" |
| Friday | November 22, 2019 | 7:30 PM | 8:20 PM | Practice | Essex Rink 1 | Peewee 2 |
| Sunday | November 24, 2019 | 7:00 AM | 8:00 AM | Game | Flynn | vs. Winchester Peewee - "AAA2" |
| Tuesday | November 26, 2019 | 6:30 PM | 7:20 PM | Practice | Essex Rink 1 | Peewee 2 |
| Friday | November 29, 2019 | 7:30 PM | 8:20 PM | Practice | Essex Rink 1 | Peewee 2 |
| Saturday | November 30, 2019 | 7:45 PM | 8:45 PM | Game | Haverhill - Gold | vs. No Andover Peewee - "AA" |
| Monday | December 2, 2019 | 7:30 PM | 8:20 PM | Practice | Essex Rink 1 | Peewee 2 |
| Wednesday | December 4, 2019 | 7:40 PM | 8:30 PM | Practice | Essex Rink 1 | Peewee 2 |
| Thursday | December 5, 2019 | 7:30 PM | 8:20 PM | Practice | Essex Rink 1 | Bantam 1, Bantam 2, Lady Chieftain U12 RED, Peewee 2 |
| Saturday | December 7, 2019 | 7:50 PM | 8:50 PM | Game | Malden | vs. Winchester Peewee - "AAA2" |
| Monday | December 9, 2019 | 7:30 PM | 8:20 PM | Practice | Essex Rink 1 | Peewee 2 |
| Wednesday | December 11, 2019 | 7:40 PM | 8:30 PM | Practice | Essex Rink 1 | Peewee 2 |
| Thursday | December 12, 2019 | 7:30 PM | 8:20 PM | Practice | Essex Rink 1 | Bantam 1, Bantam 2, Lady Chieftain U12 RED, Peewee 2 |
| Sunday | December 15, 2019 | 2:35 PM | 3:35 PM | Game | Hockeytown 3 | vs. Methuen Peewee - "AA" |
| Monday | December 16, 2019 | 7:30 PM | 8:20 PM | Practice | Essex Rink 1 | Peewee 2 |
| Wednesday | December 18, 2019 | 7:40 PM | 8:30 PM | Practice | Essex Rink 1 | Peewee 2 |
| Thursday | December 19, 2019 | 7:30 PM | 8:20 PM | Practice | Essex Rink 1 | Bantam 1, Bantam 2, Lady Chieftain U12 RED, Peewee 2 |
| Sunday | December 22, 2019 | 6:50 PM | 7:50 PM | Game | Hockeytown 4 | vs. Dorchester Peewee - "AA" |
| Monday | December 23, 2019 | 7:30 PM | 8:20 PM | Practice | Essex Rink 1 | Peewee 2 |
| Thursday | December 26, 2019 | 7:30 PM | 8:20 PM | Practice | Essex Rink 1 | Bantam 1, Bantam 2, Lady Chieftain U12 RED, Peewee 2 |
| Saturday | December 28, 2019 | 7:50 PM | 8:50 PM | Game | Hockeytown 4 | vs. Needham Peewee - "AA1" |
| Sunday | December 29, 2019 | 6:50 PM | 7:50 PM | Game | Hockeytown 4 | vs. Newburyport Peewee - "AA" |
| Monday | December 30, 2019 | 8:50 AM | 9:50 AM | Game | Hockeytown 3 | vs. Stoneham Peewee - "AA" |
| Wednesday | January 1, 2020 | 7:40 PM | 8:30 PM | Practice | Essex Rink 1 | Peewee 2 |
| Thursday | January 2, 2020 | 7:30 PM | 8:20 PM | Practice | Essex Rink 1 | Bantam 1, Bantam 2, Lady Chieftain U12 RED, Peewee 2 |
| Saturday | January 4, 2020 | 7:15 PM | 8:15 PM | Game | Haverhill - Blue | vs. Haverhill Peewee - "AA" |
| Sunday | January 5, 2020 | 6:10 PM | 7:10 PM | Game | Pingree | vs. Woburn Peewee - "AA" |
| Monday | January 6, 2020 | 7:30 PM | 8:20 PM | Practice | Essex Rink 1 | Peewee 2 |
| Wednesday | January 8, 2020 | 7:40 PM | 8:30 PM | Practice | Essex Rink 1 | Peewee 2 |
| Thursday | January 9, 2020 | 7:30 PM | 8:20 PM | Practice | Essex Rink 1 | Bantam 1, Bantam 2, Lady Chieftain U12 RED, Peewee 2 |
| Sunday | January 12, 2020 | 1:35 PM | 2:35 PM | Game | Tewksbury 1 | vs. Hollis Peewee - "AA" |
| Monday | January 13, 2020 | 7:30 PM | 8:20 PM | Practice | Essex Rink 1 | Peewee 2 |
| Wednesday | January 15, 2020 | 7:40 PM | 8:30 PM | Practice | Essex Rink 1 | Peewee 2 |
| Thursday | January 16, 2020 | 7:30 PM | 8:20 PM | Practice | Essex Rink 1 | Bantam 1, Bantam 2, Lady Chieftain U12 RED, Peewee 2 |
| Saturday | January 18, 2020 | 12:45 PM | 1:45 PM | Game | Valley Forum Ice Arena | vs. Haverhill |
| Sunday | January 19, 2020 | 3:10 PM | 4:10 PM | Game | Malden | vs. Winchester Peewee - "AAA2" |
| Monday | January 20, 2020 | 7:30 PM | 8:20 PM | Practice | Essex Rink 1 | Peewee 2 |
| Thursday | January 23, 2020 | 7:30 PM | 8:20 PM | Practice | Essex Rink 1 | Bantam 1, Bantam 2, Lady Chieftain U12 RED, Peewee 2 |
| Friday | January 24, 2020 | 7:30 PM | 8:20 PM | Practice | Massbay | |
| Sunday | January 26, 2020 | 3:50 PM | 4:50 PM | Game | Pingree | vs. North Central MA Peewee - "AA" |
| Monday | January 27, 2020 | 7:30 PM | 8:20 PM | Practice | Essex Rink 1 | Peewee 2 |
| Thursday | January 30, 2020 | 7:30 PM | 8:20 PM | Practice | Essex Rink 1 | Bantam 1, Bantam 2, Lady Chieftain U12 RED, Peewee 2 |
| Friday | January 31, 2020 | 7:30 PM | 8:20 PM | Practice | Massbay | |
| Sunday | February 2, 2020 | 10:50 AM | 11:50 AM | Game | Haverhill - Blue | vs. Hollis Peewee - "AA" |
| Monday | February 3, 2020 | 7:30 PM | 8:20 PM | Practice | Essex Rink 1 | Peewee 2 |
| Wednesday | February 5, 2020 | 7:40 PM | 8:30 PM | Practice | Essex Rink 1 | Peewee 2 |
| Thursday | February 6, 2020 | 7:30 PM | 8:20 PM | Practice | Essex Rink 1 | Bantam 1, Bantam 2, Lady Chieftain U12 RED, Peewee 2 |
| Saturday | February 8, 2020 | 8:20 AM | 9:20 AM | Game | Chelmsford | vs. North Central MA Peewee - "AA" |
| Monday | February 10, 2020 | 7:30 PM | 8:20 PM | Practice | Essex Rink 1 | Peewee 2 |
| Thursday | February 13, 2020 | 7:30 PM | 8:20 PM | Practice | Essex Rink 1 | Bantam 1, Bantam 2, Lady Chieftain U12 RED, Peewee 2 |
| Friday | February 14, 2020 | 7:30 PM | 8:30 PM | Extra-Practice | Mass Bay Hockey Center (Overtime Ice Rink) | |
| Sunday | February 16, 2020 | 5:30 PM | 6:30 PM | Game | Malden | vs. Melrose Peewee - "AA" |
| Monday | February 17, 2020 | 7:30 PM | 8:20 PM | Practice | Essex Rink 1 | |
| Wednesday | February 19, 2020 | 7:40 PM | 8:30 PM | Practice | Essex Rink 1 | Peewee 2 |
| Thursday | February 20, 2020 | 12:10 PM | 1:10 PM | Game | Haverhill - Blue | vs. Woburn Peewee - "AA" |
| Thursday | February 20, 2020 | 7:30 PM | 8:20 PM | Practice | Essex Rink 1 | Bantam 1, Bantam 2, Lady Chieftain U12 RED, Peewee 2 |
| Saturday | February 22, 2020 | 11:40 AM | 12:40 PM | Game | Malden | vs. Winchester Peewee - "AAA2" |
| Wednesday | February 26, 2020 | 7:40 PM | 8:30 PM | Practice | Essex Rink 1 | Peewee 2 |
| Thursday | February 27, 2020 | 6:30 PM | 7:20 PM | Practice | Essex Rink 1 | Peewee 2 |
| Saturday | February 29, 2020 | 9:40 AM | 10:40 AM | Game | NESC8 | vs. Assabet Peewee - "AA" |
| Wednesday | March 4, 2020 | 7:40 PM | 8:30 PM | Practice | Essex Rink 1 | Peewee 2 |
| Thursday | March 5, 2020 | 6:30 PM | 7:20 PM | Practice | Essex Rink 1 | Peewee 2 |
| Monday | March 9, 2020 | 7:30 PM | 8:20 PM | Practice | Essex Rink 1 | Peewee 2 |
| Wednesday | March 11, 2020 | 7:40 PM | 8:30 PM | Practice | Essex Rink 1 | Peewee 2 |
| Friday | March 13, 2020 | 7:50 PM | 8:50 PM | Game | Haverhill - Blue | vs. Wakefield Peewee - "AAA" |
| Monday | March 16, 2020 | 7:30 PM | 8:20 PM | Practice | Essex Rink 1 | Peewee 2 |
| Wednesday | March 18, 2020 | 7:40 PM | 8:30 PM | Practice | Essex Rink 1 | Peewee 2 |
| Monday | March 23, 2020 | 7:30 PM | 8:20 PM | Practice | Essex Rink 1 | Peewee 2 |
| Wednesday | March 25, 2020 | 7:40 PM | 8:30 PM | Practice | Essex Rink 1 | Peewee 2 |
| Thursday | March 26, 2020 | 7:30 PM | 8:20 PM | Practice | Essex Rink 1 | Bantam 1, Bantam 2, Lady Chieftain U12 RED, Peewee 2 |
| Monday | March 30, 2020 | 7:30 PM | 8:20 PM | Practice | Essex Rink 1 | Peewee 2 |
| Wednesday | April 1, 2020 | 7:40 PM | 8:30 PM | Practice | Essex Rink 1 | Peewee 2 |
| Thursday | April 2, 2020 | 7:30 PM | 8:20 PM | Practice | Essex Rink 1 | Bantam 1, Bantam 2, Lady Chieftain U12 RED, Peewee 2 |
| Monday | April 6, 2020 | 7:30 PM | 8:20 PM | Practice | Essex Rink 1 | |
| Wednesday | April 8, 2020 | 7:40 PM | 8:30 PM | Practice | Essex Rink 1 | Peewee 2 |
| Thursday | April 9, 2020 | 7:30 PM | 8:20 PM | Practice | Essex Rink 1 | Bantam 1, Bantam 2, Lady Chieftain U12 RED, Peewee 2 |