Born in Antrim, Winters first had success as an amateur, winning the Irish National senior lightweight title in 1993, fighting at the 1993 World Amateur Boxing Championships in Tampere, and winning a silver medal at the 1994 Commonwealth Games in Victoria, British Columbia, Canada.

After winning his first 11 fights he became British light welterweight champion in October 1997 after beating Carl Wright on points at the Sheffield Arena.

Winters also lost on points in September 1998 to Junior Witter,[8] but in December 1999 challenged for Ricky Hatton's WBO Inter-continental title in Liverpool.

Winters returned to the ring in 2001, and having earlier fallen out with promoter Frank Warren, joined John Breen's gym in Belfast.

[9] After having struggled to make the weight against Hatton, Winters returned at welterweight before a change of diet and training regime saw him able to drop to lightweight, and in December faced Graham Earl in an eliminator for the British title at the Wembley Conference Centre.