Howfield graduated from Columbine High School in 1984, then attended Midwestern State University in Wichita Falls, Texas from 1984 to 1985 on a soccer scholarship.

In August 1991, Howfield eventually beat out Teddy Garcia and Raul Allegre for the Oilers' kicking position after making all three field goal attempts (38, 54, 29 yards) in his preseason debut against the Dallas Cowboys.

Howfield signed practice squad contracts in following years with the Seattle Seahawks, Philadelphia Eagles, and Tampa Bay Buccaneers, but never played any regular season NFL games after 1991.

He received two disk fusions in his lower back and an entire right knee cartilage replacement, and was out of football for five years recovering from the injuries (1998 to 2002).

[11] Howfield moved to the New York Dragons later that year, and concluded the season with a league-best 66.6 conversion percentage (10 of 15), followed by a 31-yard game winner in the playoffs as time expired to advance to the quarterfinals.