[4] Born in Orange County, California, Ashe played with Beach FC - Impact before moving to Bradenton, Florida to join U.S. Soccer's residency program at IMG Academy in 2001.

On June 3, Ashe picked up his first assist as a pro on Joseph Ngwenya's goal in a 2–1 over Texas Derby rivals FC Dallas.

He made his first career start on July 10, having appeared in the previous 10 games as a sub, as the Dynamo lost to the Charleston Battery 1–0 in the U.S. Open Cup.

On July 29, Ashe made his continental debut, coming off the bench in a 1–1 draw with Monarcas Morelia in a North American SuperLiga match..

Ashe ended his rookie season making 22 appearances in MLS play, with 6 of them being starts, helping the Dynamo finish 2nd in the Western Conference.

After missing a game on May 17 due to being involved in the 2008 Toulon Tournament with the U.S. under-23 national team, Ashe returned to the Dynamo on May 28 and scored his first goal for Houston in a 2–2 draw with FC Dallas.

On July 1, Ashe played 120 minutes as Houston lost for the second straight season to the Charleston Battery in the Open Cup, this time on penalties.

Ashe made 22 appearances in the MLS regular season to help the Dynamo finish as the top seed in the Western Conference.

On July 1, Ashe came off the bench and scored one goal and assisted another to give Houston a 2–0 win over the Austin Aztex in an Open Cup match.

He started the next 2 games in the Open Cup, helping the Dynamo reach the semifinals, where they lost to Seattle Sounders FC 2–1.

On September 22 Ashe scored once and assisted on Cam Weaver's goal to give Houston a 5–1 over Árabe Unido.

During the MLS regular season Ashe made 29 appearances, 13 of them being starts, and added 3 assists, helping Houston finish 2nd in the Western Conference.

He made another appearance off the bench in the conference final vs the Los Angeles Galaxy, with the Dynamo losing 2–0 in extra time.

[11] Despite Richards scoring in the game, 1–1 draw, Ashe did good enough for Kinnear to move him to starting left back full-time.

He missed Houston's next game due to a hamstring injury, but he returned the following week and started in a 2–0 loss to Seattle Sounders FC.

Ashe made 30 starts during the regular season, with 27 of them coming at left back, as he helped Houston qualify for the playoffs.

[29] On March 5, Ashe set up Brad Davis in the 89th minute to give the Dynamo a 1–0 win over Santos Laguna in leg 1 of the 2012–13 CONCACAF Champions League quarterfinals.

On September 1 Ashe set up Adam Moffat in the 90th minute with a backheel pass to give the Dynamo a 1–1 draw with Chicago.

During the regular season Ashe made 30 appearances, including 29 starts, and recorded 2 assists as he helped Houston qualify for the playoffs.

The opening leg of the conference finals with Sporting Kansas City was a scoreless draw, but Ashe missed it due to yellow card accumulation.

[30] On July 23, the Dynamo signed DaMarcus Beasley, the starting left back for the United States at the 2014 World Cup earlier that summer.

[31] The arrival of Beasley saw Ashe's first team opportunities diminish, with him only playing 4 times in the remaining 14 games of the season.

[35] On July 14, Ashe was traded to Orlando City for a second round pick in the 2017 MLS SuperDraft and general allocation money.

[36] Ashe was acquired by Orlando City SC on July 14, 2015, in exchange for allocation money and a second round pick in the 2017 MLS SuperDraft.

[35] On November 25, Orlando City declined Ashe's contract option for the 2016 season, making him a free agent.

[42] On October 13, Ashe set up Adam Jahn in the 80th minute to give Columbus a 2–2 draw with New York City FC.

[11] Ashe was called up to the United States national team squad for friendlies against Belgium and Germany in May and June 2013, but was forced to withdraw due to injury.

[53][54] Early in his career, Ashe worked part-time as a youth soccer coach to supplement his low salary.

[55][45][56] Following Hurricane Harvey, Ashe volunteered at the Houston Food Bank and played in a charity soccer match featuring former Dynamo and Cruz Azul players.