Seymour began his football career on a Chilean reality television show called Adidas Selection Team. On the show, players from different professional clubs' youth squads were joined together to form a team to play against different schools in the Chilean Metropolitan area. The team beat all the schools it played except the last, which was San Ignacio. San Ignacio beat "Team Adidas" with five goals scored by Felipe Seymour. After that Seymour was signed by the Universidad de Chile's youth squad.
In 2005, after Adidas Reality, Seymour began his career on the youth squad of Universidad de Chile at age 17.
His Universidad de Chile professional debut was in late 2006 against Palestino.
Under the management of Arturo Salah, Seymour was on the bench for most games, but on October 21, he came off the bench in the Chilean football derby (called "Superclásico") against Colo-Colo. In 2008, his status as a substitute did not change. In Apertura 2008 he played in only five matches where he came off the bench. In Copa Chile 2008–09, he played in the starting lineup against the Santiago Wanderers in a 1–0 away loss in Estadio Regional Chiledeportes.
After the resignation of Arturo Salah and the arrival of Sergio Markarian, Seymour had more continuity in the starting lineup, and a good season for both him and the team resulted in a victory in Torneo Apertura 2009. Then with the arrival of Jose Basualdo, Seymour was frequently in the starting lineup. In Clásico Universitario he scored a goal against Universidad Católica in a 3–2 home loss.
In 2010 with the arrival of the Uruguayan coach Gerardo Pelusso, he became a key player for the club.
In Copa Libertadores 2010, he scored two long-distance goals. One took place against Flamengo in Estadio Monumental David Arellano in a 2–1 home victory in front of 30,000 spectators. The other was in a game against Alianza Lima in the last minute in the round of 16 for Copa Libertadores, when the team was losing on the global result. He was in matches on other occasions, against Huachipato on February 9 for the fourth week in Estadio Francisco Sánchez Rumoroso in a 3–0 home victory, and Cobresal on September 5 for the twenty-second week in Estadio El Cobre in a 2–1 away victory.
In May 2011, the Italian diary Gazzetta dello sport officially confirmed the transfer of the Chilean midfielder to Serie A outift, Genoa C.F.C. He has been compared with David Pizarro of Roma by the Italian press. Seymour made his Genoa debut on September 18, 2011 against S.S. Lazio, in a match won by Genoa by a score of 2–1. He played the whole 90 minutes. Seymour made 12 league appearances for Genoa in his first 5 months at the club, before being loaned to Calcio Catania for the remainder of the 2011-12 Serie A season.
On January 31, 2012 Seymour moved to Calcio Catania on a season long loan deal that expired on June 30, 2012, later went to Spezia and in 2014 signed a contract with the current Brazilian champion Cruzeiro.
After six months without a contract, the player received a very good proposal to return to south america, specifically play in Brazil. Signed with Cruzeiro Esporte Clube that comes from winning two consecutive national championships.
Felipe Seymour has been selected to play for Chile in a tournament in Kuala Lumpur, Malaysia against teams from Oceania. It is rumored that in the game against Ecuador, Felipe Seymour was nominated but not selected, though Marcelo Bielsa considered him as an alternate.