Alan worked his way through the ranks at Middlesbrough, despite being Darlington born and bred. Competitive first team appearances were not forthcoming, except for a friendly in the Anglo-Italian cup. He moved to Luton in 1997 and spent three seasons there, notching up over 80 appearances, and scoring three times. A loan spell to Colchester was made permanent, and he went onto make nearly a hundred and forty appearances, until in 2004, he moved to Leyton Orient for a season with 26 appearances. After spending the 05-06 season at Boston United (48 appearances, 4 goals), he moved to Notts County in 2006 for a season, making thirty-five appearances and scoring five times (the most he has scored for a club in one season!). His next club was Darlington, where he met a certain Tim Ryan, playing along side Celtic's assistant manager. Alan made seventy-five appearances and scored three before joining Luton Town in 2009. There was a loan spell back to Darlington, and after sixteen appearances, Luton let him go. The connection to Tim Ryan was strong enough to sway Alan into choosing Celtic, however Alan made it clear it was only ever a stop gap, and moved onto Gateshead after a few weeks.