[2] Real Esppor entered the Venezuelan Segunda División for its 2008–09 season and played its first match in the competition on 16 August 2008, a 2–1 win over Trujillanos.

In the Apertura, the team managed to stay on top of the table for most of the tournament, however losses to Caracas and Deportivo Táchira and draws against Carabobo and Trujillanos in the final five games allowed Deportivo Táchira to win the tournament on goal difference, leaving Real Esppor to settle for second place as both sides ended up tied with 36 points.

They would then set their aims on getting a berth to the Copa Libertadores through the aggregate table, which would happen in case Caracas won the Clausura, however, Zamora beat Caracas on the last matchday to claim the Clausura title and forced Real Esppor to play the Serie Sudamericana for qualification to the Copa Sudamericana, where they defeated Carabobo in the first round but were ultimately beaten to a berth by Deportivo Anzoátegui.

[1] The following season was not as successful, as the club's financial problems began to become apparent to the extent that the footballers refused to train until they received their payment.

Due to these issues, manager Noel Sanvicente resigned on 2 December 2011, before the conclusion of the 2011 Apertura tournament, in which they ended in 12th place.

[7] Later that year, Deportivo La Guaira earned its first domestic accolade by winning the 2014 Copa Venezuela under the command of manager Leo González by beating Trujillanos on penalty kicks in the final.

In that final match, played at Estadio Misael Delgado in Valencia, they faced the Group B winners Deportivo Táchira, whom they beat by a 2–0 score with goals by Martín García and Charlis Ortiz.