Howfield struggled to latch onto a professional team in his early career, with tryouts in the NFL and World League of American Football failing to lead to active signings. He eventually joined the amateur team Oklahoma City Twisters, an opportunity that was presented when he won a halftime fan kicking contest at one of their games. In August 1991, Howfield was watching the Houston Oilers' preseason game against the San Diego Chargers at The InnerUrban sports bar with his Twisters teammates, during which he proclaimed he could perform better than Houston kicker Teddy Garcia after Garcia missed two extra points. Howfield's agent contacted Oilers general managerMike Holovak, who coached his father with the New York Jets in the 1970s, for a tryout. He eventually beat out Garcia and Raul Allegre for the Oilers' kicking position after making all three field goal attempts in his preseason debut against the Dallas Cowboys. Despite making eight of ten field goals and 18 of 19 extra points to begin his pro career, Howfield struggled in October, including missing two extra points against the Cincinnati Bengals. He later missed a game-winning 33-yard field goal against the Washington Redskins, who went on to win 16–13 in overtime. He was released by the Oilers shortly after. He also played for the Philadelphia Eagles and Tampa Bay Buccaneers' practice squads but never made an active NFL roster again and was out of the NFL entirely after 1993.
In 1993, Howfield joined the Dallas Texans of the Arena Football League, where he was 7 for 27 in field goals and 19 for 23 in extra points. He moved to the Fort Worth Cavalry in 1995, where he made 10 of 29 field goals and 40 of 53 extra points. 1995 saw his first full season in the AFL with the Las Vegas Sting, during which he led the league in scoring for kickers with 120 points, a then-league-record field goal percentage at 71.4, field goals made, extra point percentage, and longest field goal. He was named Micatin Arena League Kicker of the Year and Second TeamAll-Arena for his season. He joined the Anaheim Piranhas in 1996, where he went 21 for 43 in field goals and 63 for 73 in extra points. In 1996, he led the league in field goals made with 21 and was second in FG percentage at 48.8. The following year, he had a league-best 21 field goals made with a 47.7 conversion percentage, along with 62 for 74 on extra points. Howfield was in a life-threatening car accident that cut his career short at the end of the 1997 season in Las Vegas. 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. He made a comeback in 2003 with the Tampa Bay Storm. In his first game back from the car accident, he made all three field goals. Howfield moved to the New York Dragons later that year, and concluded the season with a league-best 66.6 conversion percentage, followed by a 31-yard game winner in the playoffs as time expired to advance to the quarterfinals. He retired at the end of the 2003 season, but came back in 2004 with the Las Vegas Gladiators, where he played four games to fill in for injured kickers. He was three for five in field goals and 18 for 21 in extra points. At the time of his final retirement, he held various league and team records and stats:
All-time 2-point drop kicks: 5th
All-time field goal percentage: 15th
All-time field goal percentage in a season: 7th in 1995 with 71.4%. Arena League record at the time, lasted 9 years
* 8th 2005 with 66.7
All-time career field goal percentage: 15th
All-time field goals made: 9th
4th longest field goal ever made: 61 yards
8th all time in kicking points: 614
Tampa Bay Storm franchise record for longest playoff field goal: 47 yards
Tampa Bay Storm franchise record for field goals made in the playoffs: 2
