[1] During the 2016 MLS season the Union finished with an 11–14–9 record, which was enough for a playoff berth, the franchise's first since 2011, as the sixth seed.

The Union faced Toronto FC in the Eastern Conference knockout round, where they lost 3–1 at BMO Field.

The Union entered the fourth round of the U.S. Open Cup playing host to the Harrisburg City Islanders and won by a score of 3–2, advancing to play the New York Red Bulls in the round of 16, where a two-goal effort by Chris Pontius lifted the Union to a 2–1 victory.

The Union went on to lose 4–2 in penalties to the New England Revolution after playing to a 1-1 draw through extra time in the quarterfinals.

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