The seeding would require the Islanders to play any post-season matches on the road.

Despite being considered the underdog of the playoffs, the Islanders advanced past Commissioner's Cup winners, Orlando City SC in the quarterfinals, 4th-seeded Richmond Kickers in the semifinals, ultimately losing to Sacramento Republic in the 2014 Championship final.

The Islanders entered the 2014 U.S. Open Cup in the second round against USL PDL club FC Sonic Lehigh Valley.

Advancing through to the fourth round, the Islanders were knocked out of the tournament by their MLS affiliate Philadelphia Union in a close match where Philadelphia captain, Maurice Edu slotted an 89th-minute equalizer, bringing the match to extra time.

Through extra time, Pennsylvania native, Andrew Wenger, struck twice advancing the Union with a score 3–1.