In 2016, the Union would acquire Chris Pontius from D.C. United, Surinames midfielder Roland Alberg, and Brazilian right midfielder Ilsinho. They would also acquire U.S. international Alejandro Bedoya in the summer transfer window. The Union would also add key players from the 2016 MLS SuperDraft including Josh Yaro, Keegan Rosenberry, and Fabian Herbers. The 2016 season saw success from Goalkeeper Andre Blake who later would win the 2016 MLS Goalkeeper of the Year Award. The Union were in constant playoff contention, however went 0–5–2(W-L-T) in the final 7 matches of the regular season. The Union would still reach the playoffs for only the 2nd time in team history, beating out New England Revolution on goal differential. The Union were beaten 3–1 in the Knockout round of the 2016 MLS Cup Playoffs by Toronto FC. The Union were unable to build on their 2016 success, finishing with the same record but still missing the playoffs in 2017. Despite failing to make the playoffs, Curtin was announced to retain his head coach position for the 2018 season. Ahead of the 2019 season, Union Sporting Director, Ernst Tanner, announced that Curtin would be retained for the upcoming season on a one-year extension. By July of that season, the Union reach first place in the Eastern Conference and hitting the club's best start to a season. This success lead to the club announcing Curtin signed a two-year contract extension, to remain head coach through the 2021 season. First trophy and success The 2020 season was the most successful to date for the Union. Despite disruptions from the COVID-19 pandemic, the Union reached the semi-final of the MLS is Back Tournament and went on to win their first trophy finishing top of the league standings and earning the 2020 Supporters' Shield. The team's performance over the season earned Curtin his first Sigi Schmid Coach of the Year Award. Winning the Supporter's Shield earned the Union their debut in the CONCACAF Champions League, where the Union earned their first international win against Deportivo Saprissa; a victory that marked Curtin's 100th win as head coach of the club. Within two days prior to the Union's first ever conference final match in team history, it was reported that 11 players, including six starters had to undergo the league's COVID-19 protocol. Philadelphia lost to eventual champions New York City FC 2–1. It was later stated that it would've been