Benjamin had trials with Cheltenham Town, Gillingham and Bournemouth at the start of the 2008–09 season, but failed to earn a contract at any of the three clubs. Bournemouth manager Jimmy Quinn said of the player, "He's not what I'm looking for, he's probably past his sell-by date." On 10 October 2008, Benjamin signed for Northwich Victoria, but was released three weeks later as part of cost-cutting measures. He then made one appearance at Hednesford Town in the Northern Premier League Premier Division, after a few games for the club he was released. A couple of weeks later, Benjamin moved further down the non-league ladder to sign for his home town club Wellingborough Town in the United Counties Football League. He scored on his debut in the 2–2 Boxing Day draw with Raunds Town.