After winning the Jack Dyer Medal in 2003, Coughlan was hampered in 2004 by osteitis pubis, however he returned in 2005 and averaged more than 22 touches a game and finished the season ranked third in the competition for tackles (123) and sixth for handballs (235).

After a solid start to his 2006 campaign, Coughlan fell awkwardly and ripped the anterior cruciate ligament (ACL) inside one of his knees in round 12 against Hawthorn, ending his season.

Following his successful comeback, columnist for The Age and Richmond teammate Nathan Brown described Coughlan as a very popular player and "the rarest individual I have ever met...in my 13 years of playing football".

On 11 April 2010, Coughlan made his debut with St Kevin's Old Boys in Premier B of the Victorian Amateur Football Association (VAFA).

In a stunning display, he amassed 45 possessions as he joined forces with great friend and former Melbourne Demons player Luke Williams (51 senior AFL games) to help deliver a hard-fought 24-point victory over arch-rivals St Bernards.