I have a tricky situation and want to know from the forum I had a tier 1 General visa stamped on 28th Jan 2009 which was valid for 3 years. I was based outside UK for 2009 and just made a 5 day visit to UK. On 2nd Mar 2010 I entered UK on that Tier 1 General and started working on a project in UK ...

Since your friend wants to apply on the 9th July 2014, his chart will look something like this
Year 1 - 9th July 2014 - 10th July 2013
Year 2 - 9th July 2013 - 10th July 2012
Year 3 - 9th July 2012 - 10th July 2011
Year 4 - 9th July 2011 - 10th July 2010
Year 5 - 9th July 2010 - 10th July 2009