Flynn was third in a trio of players signed in May 2003, with the close season only three weeks old. But it signalled Graham Westley‘s intent; the Boro’ manager aiming to further refine his squad after salvaging Conference security when he took over. The left-back joined us on a free from Hertfordshire rivals Barnet. His main role? To cover a void left by the departing Stuart Fraser.
It was hoped that the Conference experience Flynn picked up at Underhill would be a useful asset. That was especially the case as he went up against Justin Gregory for the left-back spot. But Flynn was to lose out and found his opportunities at Broadhall Way stifled. With a quarter of a century’s worth of appearances behind him, Flynn moved on after being deemed surplus to requirements.