East Islip and pitcher John Dondero fell 8-2 to Longwood on May 17 in the first round of the Suffolk County AA playoffs.  
In the May 18 Suffolk loser's bracket game, East Islip was shut out by West Islip, 1-0. EI pitcher Ken Rotunno threw a 2-hitter.

East Islip’s boys tennis team lost 4-3 to Floyd on May 16 in the first round of the Suffolk County playoffs. Raul Ramos and Andrew Loizides were defeated by A.J. Taranto and Jason Lin 6-3, 6-4 in the deciding third doubles match.

The boys varsity track and field team had another excellent showing at the annual Freshman Sophomore Championships held on May 16 at Longwood High School. The team was led by its freshman athletes, who scored a total of 31 points and tied for third place overall in the freshman division. Standout freshmen for this meet included triple-medalist Zach Acocella (third place in long jump, second place in 400-meter and first place in triple jump), Alex Russo (third place in triple jump) and Tom Koppelman (sixth place in the 400-meter intermediate hurdles).
Other noteworthy EI athletes were sophomores Jessie Friel (second place overall in the pole vault) and Evan Barnes (jumping a personal best 18'10" in the long jump).
“For many of our freshman and sophomore athletes this marked the end of their season,” said coach James Connell. “For most athletes who competed yesterday, they were running and jumping their personal bests. As a coach you can't ask for anything better than that!”

East Islip beat West Islip 8.5-0.5 on May 16 at at the Timberpoint Red Course, led by Kim Schmidt’s 9-over-par 45.

In the first round of the playoffs, East Islip came away with an impressive 16-9 victory against Patchogue-Medford on May 18, led by Victoria Gregson’s seven goals. Other EI scorers were Lisa Olen (3 goals, 1 assist), Elizabeth Vetter (3 goals), Nicole Levy (1 goal, 4 assists), Carlee Ancona (1 goal. 4 assists), Shannon Cummings (1 goal, 2 assists) and Jackie Niciforo (2 assists).
EI goalies Krista Ancona and Lee-Ann Salim each made 3 saves.
East Islip edged Northport 8-7 on May 21 in the second round, sparked by Krista Ancona’s 8-save performance. Scorers were Levy (2 goals, 2 assists), Niciforo (2 goals, 1 assist), Gregson (2 goals), Vetter (1 goal, 1 assist) and Olen (1 goa

East Islip’s softball team lost 6-5 to Whitman on May 14. Courtney Blake was EI’s losing pitcher.
EI bounced back on May 16, clobbering Smithtown East by a lopsided 15-0 score. Blake was the winning pitcher , Kelsey Fileccia went 4-for-4 with 3 runs and Alexa Martone went 3-for-4 with 2 runs.
On May 17, East Islip clinched the League III title by beating Newfield 3-1. Blake pitched a 3-hitter with 7 strikeouts for her 50th career victory. The senior went 2-for-2 with 2 runs. Shelby Heyward went 2-for-3 with one RBI.