| Date | Time | Team Level | Type | Status | Home/Away | Opponent | Result | Score | Details | Site | Transportation |
| SAT 4/2 | 2:00 p.m. | Varsity | League | Normal | Home | Stratford | Loss | 2-3 | | Darien High School-DHS Baseball - Varsity Field | |
| MON 4/4 | 4:30 p.m. | Varsity | League | Normal | Home | NewFairfield | Loss | 2-3 | | Darien High School-DHS Baseball - Varsity Field | |
| MON 4/11 | 4:00 p.m. | Varsity | League | Normal | Home | WilburCross | Win | 8-1 | | Darien High School-DHS Baseball - Varsity Field | |
| TUE 4/12 | 4:00 p.m. | Varsity | League | Normal | Away | Cheshire | Loss | 0-2 | | Cheshire High School-Baseball Diamond | |
| THU 4/14 | 2:30 p.m. | Varsity | League | Normal | Home | Norwalk | Loss | 1-7 | | Darien High School-DHS Baseball - Varsity Field | |
| SAT 4/16 | 11:00 a.m. | Varsity | League | Normal | Away | Stratford | Loss | 2-10 | | Penders Field-Penders Field - Stratford | |
| MON 4/18 | 4:00 p.m. | Varsity | League | Normal | Away | Westhill | Loss | 0-6 | | Westhill High School-Varsity Baseball Field | |
| WED 4/20 | 4:00 p.m. | Varsity | League | Normal | Away | Trumbull | Loss | 3-6 | | Trumbull High School-Varsity Baseball Field | |
| FRI 4/22 | 4:00 p.m. | Varsity | League | Normal | Home | FairfieldLudlowe | Loss | 2-3 | | Darien High School-DHS Baseball - Varsity Field | |
| MON 4/25 | 6:00 p.m. | Varsity | League | Normal | Away | BrienMcMahon | Loss | 2-3 | | Brien McMahon High School-Pride Field | |
| WED 4/27 | 4:00 p.m. | Varsity | League | Normal | Home | BridgeportCentral | Win | 12-1 | | Darien High School-DHS Baseball - Varsity Field | |
| FRI 4/29 | 4:30 p.m. | Varsity | League | Normal | Away | Staples | Loss | 1-7 | | Staples High School-Baseball Diamond | |
| TUE 5/3 | 4:30 p.m. | Varsity | League | Normal | Away | Greenwich | Loss | 0-1 | | Greenwich High School-Baseball Field | |
| WED 5/4 | 4:00 p.m. | Varsity | League | Normal | Home | Danbury | Loss | 3-5 | | Darien High School-DHS Baseball - Varsity Field | |
| THU 5/5 | 4:00 p.m. | Varsity | League | Normal | Home | StJoseph | Win | 7-4 | | Darien High School-DHS Baseball - Varsity Field | |
| MON 5/9 | 4:00 p.m. | Varsity | League | Normal | Home | NewCanaan | Loss | 4-12 | | Darien High School-DHS Baseball - Varsity Field | |
| WED 5/11 | 4:00 p.m. | Varsity | League | Normal | Away | Ridgefield | Loss | 0-3 | | Governor Field | |
| THU 5/12 | 4:00 p.m. | Varsity | League | Normal | Home | Stamford | Win | 9-3 | | Darien High School-DHS Baseball - Varsity Field | |
| WED 5/18 | 4:00 p.m. | Varsity | League | Normal | Away | FairfieldWarde | Loss | 6-7 | | Fairfield Warde High School-Baseball Diamond | |
| THU 5/19 | 4:00 p.m. | Varsity | League | Normal | Home | Wilton | Loss | 1-2 | | Darien High School-DHS Baseball - Varsity Field | |