Norwich caretaker manager Bryan Hamilton moved swiftly after his appointment to sign his namesake Des Hamilton from Newcastle on loan until the end of the 1999/2000 season. Arriving on 21st March along with Newcastle colleague Garry Brady, Des, real name Derrick, had been transfer listed by Newcastle boss Bobby Robson. Originally at Bradford, Des came through the youth team at Valley Parade to establish himself as one of the best defenders in the Nationwide League. After 88 games for Bradford, he signed for Kenny Dalglish's Newcastle in March 1997 for £1.375million. However he failed to establish himself in the Newcastle first team despite playing in a midfield role. Loan spells at Sheffield United and Huddersfield followed before his move to Carrow Road.

Des made his debut for Norwich in the 2-2 draw at QPR on 25th March 2000. Des and Garry Brady returned to Newcastle at the end of the 1999/2000 season with Norwich unlikely to sign them according to comments made by manager Bryan Hamilton in the Eastern Daily Press. This will upset fans who thought Des added bit and commitment to the Norwich midfield / defence.

The Sunday People reported on 25th June 2000 that new Bradford City manager Chris Hutchings wants to make the versatile Hamilton his first signing for Bradford with a £200,000 move for the player who was unwanted at Newcastle. Des was later named as a makeweight in an exchange for Lee Clark of Fulham. Des eventually joined Tranmere on loan during the last week of October 2000. This agreement was renewed in January 2001 to last for three months but not before Newcastle attempted to use Des as makeweight in an exchange deal with Sheffield Wednesday for Giles de Bilde. Des returned to Newcastle in mid March 2001 following John Aldridge's resignation as Tranmere manager.

Des was linked with a transfer to Cardiff City on May 20th 2001 by The Sunday People which became even more likely two days later when he was released by Newcastle. Although Tranmere showed an interest, Des passed a medical on June 8th and signed a four year contract with Cardiff on July 1st when his contract with Newcastle expired.

On Transfer Deadline day 2003 (March 27th), it was reported that Des had joined Grimsby on loan. However the Mariners had used up their quota of loan signings and so Des had to return to Ninian Park and compete for a first team place. Following Cardiff's promotion to Division One in the Second Division play-offs, manager Lennie Lawrance informed Des and colleague Leyton Maxwell that they were free to leave Ninian Park. However they are both able to stay on and claim a wage under their contract unlike the 10 players released at the time, including Mark Walton, Fan Zhiyi, Gareth Ainsworth and Leo Fortune-West. The following month saw Des training with Grimsby and he signed for the Mariners in July 2003.

Des made 24(7) appearances for the Mariners but his form was poor - a match report of his final game, against Bournemouth, described his misplaced passes, mistimed tackles and general lethargy. New Grimsby manager Nicky Laws had enough and replaced Des with Walsall's Jamie Lawrance. Des was released on a free transfer and signed for Conference side Barnet on non-contract terms.

After leaving Barnet, Hamilton returned to his native Bradford and is playing for Campion in the West Riding County Amateur League. He also played in May 2007 at the new Wembley in the FA Umbro Fives final for Bradford side NBK

He joined Eccleshill Town of the Northern Counties East League as Assistant Manager on July 28th 2017.