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Bailey died on 11 March 2014, following a battle with lung cancer.

In a statement released by Adelaide on 27 November 2013, it was revealed that Bailey was suffering from cancer and was on indefinite leave. He never returned to work, though he did visit the club in late 2013 and early 2014 during pre-season training before his untimely death in March.

The 2011 season saw the Demons experience great fluctuations in form. Starting the season with a draw against Sydney, the team was well beaten by Hawthorn in the second round, despite leading at half time. Consecutive victories followed, with a narrow win over the Brisbane Lions, and league newcomers Gold Coast by 90 points. Following a bye, the club suffered a 54-point defeat at the hands of West Coast, before bouncing back the following week, thrashing Adelaide by 96 points, recording their biggest ever victory against them. It was also their biggest win under Dean Bailey to date. Three losses followed, followed by a surprise victory over Essendon.

On 4 October 2011, Bailey was appointed to the Adelaide Football Club in a new role as a strategy and innovation coach.

The 2010 season began with a first round-loss to Hawthorn by 56 points in which the playing group and Bailey were criticised in the media for their on-field performance. But the Demons bounced back in their second game of the season, losing to eventual premier Collingwood by just one point. Round three saw the Demons chalk up their first victory of the season, a 16-point victory over the Adelaide Crows. This was followed by big victories over Richmond and the Brisbane Lions, the latter considered to be a major upset at that point of 2010, as the Lions were undefeated at the time, and fielded big name players including Brown and Fevola.

The 2009 season started with three losses for the Demons before an inspiring and unexpected win by eight points against Richmond in their round four clash at the MCG. At the mid-way point of the 2009 season, the Demons sat last on the ladder with one win and eleven losses, but Bailey retained his commitment to youth and gave many youngsters on Melbourne's list valuable experience over the first half of the year. The club finished the 2009 season with four wins and 18 losses and finished last on the ladder for the second year running.

Eighteen months after his sacking as Melbourne coach, an investigation into the club's 2009 season found Bailey and then football manager Chris Connolly guilty of "acting in a manner prejudicial to the interests of the competition". This related most specifically to a meeting in July 2009, which became known colloquially as "the vault", in which Connolly allegedly openly discussed the potential benefits to the club of tanking. Bailey, then an assistant coach at the Adelaide Crows, was banned from coaching for the first sixteen rounds of the 2013 season, meaning he could not engage with any players during his suspension.

Season 2008 started badly for Bailey, with the Demons losing their first six games by lopsided margins before winning its first match of the season against Fremantle in round seven.

Things did not get better, as the Demons lost the next six games, however they won their second game in Round 14 against Brisbane. Then they lost the next five games and won their third game in Round 20 against West Coast. Melbourne finished 16th at the end of the 2008 season, claiming the wooden spoon with three wins and 19 losses.

At the end of the 2007 season, he was appointed as the new senior coach of the Melbourne Football Club for the 2008 season.

Despite elevated expectations the Demons then went on to lose their next three games. A narrow victory over Port Adelaide in round 9 however gave fans something to celebrate. Again the club suffered several more losses following the win, as well as a nail biting draw to Collingwood in the annual Queens Birthday Clash. The club found some form again in the following weeks, beating Essendon in round 15, narrowly losing to Fremantle in round 16 (after a huge comeback) and winning again in round 17, thrashing 2005 premiers Sydney by 73 points. A 10-point win over struggling Brisbane at the Gabba and then Richmond at the MCG followed. Ultimately the Demons finished 12th on the ladder at season's end, a somewhat huge improvement from the past two seasons.

He joined the Port Adelaide Football Club in 2002 as an assistant coach, a position he held in their 2004 premiership season.

After retiring as a player he became a development coach at the Essendon Football Club and helped the club to their 2000 premiership.

Dean Bailey (18 January 1967 – 11 March 2014) was an Australian rules football player and coach. He played for the Essendon Football Club and was the senior coach of the Melbourne Football Club, as well as an assistant coach at Essendon and Port Adelaide and the Strategy & Innovation Coach at the Adelaide Football Club (Adelaide Crows). Bailey died of lung cancer on 11 March 2014.