Dean Howell's career began as a trainee at Notts County where he spent two years and made one substitute appearance. He was loaned out to Spalding United during his time at Notts County but his performances there didn't persuade County to keep him and he signed for Dario Gradi's Crewe Alexandra before the start of the 2000/2001 season.

He found his first team opportunities at Crewe as hard to come by as they were at Notts County and he was one again loaned out to another club, this time Rochdale where he spent the last two months of the season. He was given his first league start at Rochdale and managed three appearances before the end of his loan spell. Crewe decided not to retain his services and he was released on a free transfer.

Howell later made the move into non league football with Southport where he made over 50 appearances for the Sandgrounders, scoring four goals in the process. When Southport were relegated from the Nationwide Conference at the end of the 2002/2003 season Howell was given a free transfer and Jim Harvey brought him back into Conference football with Morecambe. Despite him playing primarily as a left back at Southport, Howell was signed as a replacement for Lee Elam on the left hand side of midfield after Elam's shock departure to Halifax Town.

He impressed during Morecambe's pre season, causing defences all sort of problems with his blistering pace and deadly crossing ability, but he struggled to reproduce his pre season form once the Nationwide Conference season got underway. He scored his first goal for the club against his home town club Burton Albion in a 2-1 victory for the Shrimps at the end of August.

After a season of poor form with only brief glimpses of the ability he showed in pre season Morecambe decided to offload Howell. He was snapped up by Yorkshire club Halifax Town where he joined up with former Morecambe team mate Ian Dunbavin.