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In January 2017 he signed for Major League Soccer club San Jose Earthquakes joining Panama teammate Aníbal Godoy. Cummings suffered a broken leg at his home in March. Following this injury, he was listed as out for the season in May without having made a single appearance for San Jose. Cummings made his MLS debut on 3 March 2018, in San Jose's season-opening 3–2 victory over Minnesota United.

Cummings said in February 2018 that he hoped to make a successful comeback from his injuries and perform well for San Jose, for which he did not appear in 2017, and translate a strong club appearance into call-ups for Panama's March friendlies and eventual 2018 FIFA World Cup appearance, the first in national history. He was called up to the squad for friendlies against Denmark and Switzerland on 22 and 27 March, respectively, alongside San Jose teammate Aníbal Godoy.

In May 2018 he was named in Panama’s preliminary 35 man squad for the 2018 World Cup in Russia.

Cummings scored his first international goal on November 20th, 2018. However, this goal was cancelled by an own goal he scored on September 8th, 2019 against Bermuda.

At the start of 2017, Cummings was named to the 2017 Copa Centroamericana Best XI for his performances in the January tournament, which qualified Panama for the 2017 CONCACAF Gold Cup. In February, he received a call-up for Panama's 2018 FIFA World Cup qualification matches against Trinidad and Tobago and the United States on 24 and 28 March, respectively, but was called home from camp by San Jose due to injury issues that the club did not wish to aggravate. These injuries persisted throughout the year and prevented him from taking part in the Gold Cup and in Panama's September World Cup qualifiers as well.

In January 2015 he signed for Categoría Primera A club Independiente Santa Fe.

In January 2014 he joined Peruvian outfit Juan Aurich to play alongside compatriot Luis Tejada

Cummings was part of the Panama U-20 squad that participated in the 2011 CONCACAF U-20 Championship where he help his nation qualify to the 2011 FIFA U-20 World Cup in Colombia.

His senior international debut for Panama came on 7 September 2010 against Trinidad and Tobago, in a Friendly match played in Panama City. In 2011, he was called up by Julio Dely Valdés to play the 2011 CONCACAF Gold Cup.

In 2009, he signed for Liga Panameña de Fútbol club Árabe Unido where he made 22 appearances. In 2011, he signed for Uruguayan Primera División club River Plate on loan.

Harold Oshkaly Cummings Segura (born 1 March 1992) is a Panamanian footballer who currently plays as a defender for the Unión Española and Panama national football team.