Penilla joined
Barcelona in January 2013 from
Deportivo Quito, one year after he left
ESPOLI for Deportivo Quito. In his first season with
Barcelona he scored six goals out of 32
league games. On December 24, 2014, it was confirmed that Penilla would join
Pachuca.
New England Revolution On January 23, 2018, Penilla was loaned to the
New England Revolution of
Major League Soccer. He made his Revolution debut (and first start) on March 3, in the
2018 New England Revolution season opener, a 2-0 loss to the Philadelphia Union. He made his home debut and notched his first Revolution assist the following week in a 2-1 win over the Colorado Rapids, setting up Diego Fagundez's 48th minute goal. He scored his first goal for the Revolution on March 31 in a 2-0 win over the Houston Dynamo. Penilla recorded the fastest brace in club history on May 12, scoring in the 4th and 7th minutes of the club's 3-2 victory over Toronto FC. Penilla led the Revolution in appearances (33), starts (33), and goals (12) during the 2018 season, additionally notching 7 assists. He was named to the MLS Team of the Week five times during the season. Penilla was named
Midnight Riders Man of the Year, Revolution Player's Player of the Year, and Revolution team MVP, winning the club's golden boot. New England made his move permanent at the end of their 2018 season. In the
2019 New England Revolution season, Penilla recorded 6 goals and 8 assists. He made his 50th MLS appearance on July 17, a match in which he notched two assists coming off the bench as a 68th minute substitute against the Vancouver Whitecaps in a 4-0 win. In the abbreviated
2020 New England Revolution season, Penilla made 17 appearances, recording four assists. He suffered a fracture to his left foot in the Revolution's October 11 2-1 win over New York City FC, requiring him to undergo surgery and miss the remainder of the season. The Revolution declined his contract option on December 8, 2020.
C.D. Cuenca In June 2021, Penilla signed for
Ecuadorian Serie A club
C.D. Cuenca. ==International career==