| Date | Time | Team Level | Type | Status | Home/Away | Opponent | Result | Score | Details | Site | Transportation |
| SAT 4/1 | 3:00 p.m. | Varsity | League | Normal | Home | WilburCross | Win | 10-0 | | Darien High School-DHS Baseball - Varsity Field | |
| MON 4/3 | 4:30 p.m. | Varsity | League | Normal | Home | NewFairfield | Win | 11-4 | | Darien High School-DHS Baseball - Varsity Field | |
| WED 4/5 | 4:15 p.m. | Varsity | League | Normal | Away | Stratford | Loss | 2-3 | | Penders Field-Penders Field - Stratford | |
| SAT 4/8 | 11:00 a.m. | Varsity | League | Normal | Home | Sheehan | Win | 7-3 | | Darien High School-DHS Baseball - Varsity Field | |
| THU 4/13 | 1:00 p.m. | Varsity | League | Normal | Home | Stratford | Win | 11-1 | | Darien High School-DHS Baseball - Varsity Field | |
| FRI 4/14 | 4:00 p.m. | Varsity | League | Normal | Away | Norwalk | Win | 5-4 | | Nathan Hale MS-Callahan Complex at Nathan Hale Upper | |
| MON 4/17 | 4:00 p.m. | Varsity | League | Normal | Home | Westhill | Loss | 11-8 | | Darien High School-DHS Baseball - Varsity Field | |
| WED 4/19 | 4:00 p.m. | Varsity | League | Normal | Home | Trumbull | Loss | 10-0 | | Darien High School-DHS Baseball - Varsity Field | |
| FRI 4/21 | 4:00 p.m. | Varsity | League | Normal | Away | FairfieldLudlowe | Win | 8-3 | | Kiwanis Field-Baseball Diamond | |
| MON 4/24 | 4:00 p.m. | Varsity | League | Normal | Home | BrienMcMahon | Loss | 5-2 | | Darien High School-DHS Baseball - Varsity Field | |
| WED 4/26 | 4:00 p.m. | Varsity | League | Normal | Away | BridgeportCentral | Win | 15-4 | | Bridgeport Central High School-Baseball Diamond | |
| FRI 4/28 | 4:00 p.m. | Varsity | League | Normal | Home | Staples | Loss | 2-1 | | Darien High School-DHS Baseball - Varsity Field | |
| MON 5/1 | 4:30 p.m. | Varsity | League | Normal | Home | Greenwich | Loss | 4-3 | | Darien High School-DHS Baseball - Varsity Field | |
| WED 5/3 | 4:15 p.m. | Varsity | League | Normal | Home | Danbury | Loss | 10-4 | | Darien High School-DHS Baseball - Varsity Field | |
| FRI 5/5 | 4:00 p.m. | Varsity | League | Normal | Away | StJoseph | Loss | 13-5 | | St. Joseph High School-Baseball Diamond | |
| MON 5/8 | 4:00 p.m. | Varsity | League | Normal | Away | NewCanaan | Loss | 4-3 | | Mead Park-Baseball Field | |
| WED 5/10 | 4:00 p.m. | Varsity | League | Normal | Home | Ridgefield | Win | 2-0 | | Darien High School-DHS Baseball - Varsity Field | |
| THU 5/11 | 4:00 p.m. | Varsity | League | Normal | Away | Stamford | Loss | 6-5 | | Stamford High School-SHS Baseball Diamond | |
| MON 5/15 | 4:15 p.m. | Varsity | League | Normal | Away | Wilton | Win | 4-2 | | Wilton High School-Varsity Baseball Field | |
| WED 5/17 | 4:00 p.m. | Varsity | League | Normal | Home | FairfieldWarde | Loss | 6-2 | | Darien High School-DHS Baseball - Varsity Field | |