[3] In late 1995, Connolly joined the Hawthorn Football Club as reserves coach for the 1996 season.

Despite an indifferent start, and with intense scrutiny on Connolly's coaching, Fremantle stormed home, winning a club record nine games in a row and finishing third at the end of the 2006 season.

Fremantle president Rick Hart publicly stated that making finals would be a major factor in Connolly retaining the senior coaching post.

[18] In 2013, an investigation into Melbourne's 2009 season found Connolly and former senior coach Dean Bailey guilty of discussions not in the best interests of the AFL.

This occasion became known colloquially as 'the vault' meeting, in which Connolly allegedly openly discussed the potential benefits to the club of tanking.

However, following the resignation of both the CEO and president, Connolly was sacked by the Melbourne Football Club in October 2013.

He has also provided special comments on ABC Radio and AFL Live, as well as working with Croc Media on the Footy WA television show.

In 2014, Connolly also became a founding partner of Advanced High Performance (advancedhp.com.au) with Mark Campbell, Martin Sperring and Wayne Oswald, specialising in designing software and support programs for community clubs, administrators, coaches and players.

CLUBMAP (clubmap.com.au) is joining major community groups and commercial partners to work with organisations from 65 sports; 7500+ volunteer administrators from 3000+ clubs across Australia and internationally.

AFL senior players produced: Ben Dixon, Angelo Lekkas, Luke McCabe, Jade Rawlings, Jonathan Hay, Rayden Tallis, Brad Scott.

2002 - took over the coaching reins following Fremantle's 2001 wooden spoon season and the declaration that the club had a $8 million debt.

Then awarded the Con Regan medal, which recognises those who 'have made an extraordinary, inspirational and personal contribution' to the Fremantle Football Club.