Paul Gascoigne (Kettering Town)
Sadly, Gascoigne’s managerial career – all 39 days of it – mirrored his playing career. He signed for Conference North side Kettering Town, and promisingly made pledges to be a long-term appointment, before disappearing very abruptly into the managerial wilderness, leaving fans to wonder what might have been. Gazza was sacked little over a month into the job, with the board suggesting that the former England international had been drinking daily throughout his tenure.