2019: In 2019, Segura saw his playtime increase as he made a career-high 33 appearances (19 starts). The 26-year-old put together a solid season as he finished with three goals and two assists. Throughout the season, Segura showed his versatility as Head Coach ben Olsen played him all over the field. The midfielder was named to MLS Team of the Week after he recorded his first multi-goal game against the Chicago Fire on May 29. Segura's two goals helped United secure a 3-3 tie after they fell behind 2-0 early in the match.
2018: In his first year with United, Segura made 23 appearances (14 starts) compiling 1,293 minutes on-the-field. He scored his first goal for the club in the opening minute during a 1-0 win against Columbus Crew SC on Apr. 14 at Navy-Marine Corps Memorial Stadium. After sustaining an injury in May, Segura returned to the team as a substitute in the 1-0 loss to the New York Red Bulls on Jul. 25. On Sept. 12, Segura rediscovered his scoring form when he latched on to a 65th-minute equalizer against Minnesota United. His equalizer led to a game-winner from Darren Mattocks in the 69th minute. The Costa Rican recorded his first MLS assist in the 4-1 win against Portland on Aug. 15 when he supplied Darren Mattocks with a stoppage time goal (90’+1’). During his time in the District, Segura has earned four caps for Costa Rica in international friendlies against Tunisia, Mexico, Colombia, and United States.
2014-2018: Segura made his professional debut for Deportivo Saprissa on Jan. 19, 2014 in a 2-2 draw with AD Carmelita. He went on to score 14 goals and record four assists in 124 appearances for the club from 2014-2018. He spent the 2014/2015 season with CS Uruguay de Coronado and scored three goals and recorded an assist in 39 appearances.
Segura began his career with Deportivo Saprissa in the Costa Rican first tier. Segura made his professional debut for Saprissa on Jan. 19, 2014 in a 2-2 draw with AD Carmelita. He went on to score 14 goals and added four assists in 124 appearances for the club from 2014- 2018. He spent the 2014/2015 season on loan with CS Uruguay de Coronado where he scored three goals and recorded an assist in 39 appearances.
Ulises Segura has made ten appearances for the Costa Rican National team. Segura made his international debut in a 3-0 win over Belize on Jan. 15, 2017. During the 2017 CONCACAF Gold Cup, the midfielder appeared in two matches for Costa Rica. In the final match of the group stage, Segura helped his country advance to the quarterfinals with a 3-0 victory over French Guiana. During the quarterfinals, Segura came off the bench in the 1-0 victory over Panama to help his team secure a place in the semi-finals.
United signed Segura on a permanent transfer from Deportivo Saprissa on Dec. 21, 2017, pending receipt of his P1 Visa and International Transfer Certificate and traded $50,000 in General Allocation Money to New York City FC in exchange for the rights to sign Segura.