Roach played for Watford's youth team,[1] and Milton Keynes Dons in the 2003–04 season, before having a trial at Aldershot Town in July 2004.
[2] Aldershot manager, Terry Brown commented on Roach's performance in a friendly against Maidenhead United; "I think Darryl did well, to be fair the boy's hardly trained and we've come in and put him into two games.
[3][4] Roach then joined Southern League Division One East club Tilbury in February 2005,[5] before later moving onto Wingate & Finchley in March 2005.
[8] He made his debut against Belize on 15 June, in their home fixture, which was played at Ato Boldon Stadium in Couva, Trinidad and Tobago.
[9] He played again in the away tie which was at held at Estadio Olímpico Metropolitano in San Pedro Sula, Honduras, but could not prevent Montserrat losing 3–1 and overall 8–3 on aggregate.