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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 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 (60%) in field goals and 18 for 21 (85.7) in 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 (1998 to 2002). 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 (10 of 15), followed by a 31-yard game winner in the playoffs as time expired to advance to the quarterfinals.

He joined the Anaheim Piranhas in 1996, where he went 21 for 43 (48.8%) in field goals and 63 for 73 (86.3%) 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.

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 (20 of 28), field goals made (20), extra point percentage (91 percent), and longest field goal (61 yards against the Miami Hooters). He was named Micatin Arena League Kicker of the Year and Second Team All-Arena for his season.

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 (25.9%) in field goals and 19 for 23 (82.6%) in extra points. He moved to the Fort Worth Cavalry in 1995, where he made 10 of 29 (34.5%) field goals and 40 of 53 (75.5%) extra points.

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 manager Mike 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.

Howfield played six years in the National Football League as a placekicker: Miami Dolphins in 1987, Seattle Seahawks from 1988–1989 (signed to the practice squad for both years), Denver Broncos in 1990, Houston Oilers in 1990–1991, Philadelphia Eagles in 1992 and Tampa Bay Buccaneers in 1993. He led the Oilers in scoring in 1991.

Howfield graduated from Columbine High School 1984, then attended Midwestern State University in Wichita Falls, Texas from 1984 to 1985. He transferred to the University of Tennessee in 1986 to begin his placekicking career, graduating in 1987.

Ian Michael Howfield (born June 4, 1966) is a former American football placekicker who played in the National Football League (NFL) and Arena Football League (AFL). Howfield, who played college football at the University of Tennessee, is the son of former NFL placekicker Bobby Howfield.