[4] Soon after he joined Conference Premier side Woking on a similar deal until the end of the season, making a further eight appearances.
[5][6] Despite top scoring for the academy with seven goals from 14 games during 2008–09, he left Reading at the end of the season having not been offered a professional contract.
[7][9] He suffered a serious knee injury during his time with the club and failed to make an appearance for the first-team, joining Eerste Divisie side SC Cambuur on loan in March 2011.
[1][11] In August 2013 he joined Southern League Premier Division side Cambridge City on non-contract terms.
[17] After less than three months with Hayes & Yeading, Bossman returned to Cambridge City in November on a game-by-game basis,[18] citing "personal reasons" for the move.