Paul Jewell was seen as the man to bring the good times and Premier League football back to Portman Road. Right now it appears as though League One football is closer than England's top flight.
So what is wrong in East Anglia? The club is owned by ambitious businessman Marcus Evans, who took over the club in 2007 and wiped out the club's debts.
He appointed Roy Keane as manager, but it was an unstable alliance, with Keane's man-management skills called into question by his players, and was sacked in 2011.
Keane was not a man renowned for putting his arm around the shoulder of underperforming players, and his hard-edged management style certainly put a few noses out out of joint, although fortunately not literally.
At one point Keane called in a shrink to help the mental attitude of players, but it did not help, the club sunk to 19th and he was dismissed before it got worse.
But Keane's worst action was one they are still paying for, he sold Jordan Rhodes before he could even make an impact at the club. Rhodes was snapped up for £8 million from Huddersfield by Blackburn this summer, and will lead Rovers' promotion push.
As for Paul Jewell, the man who excelled with Wigan arrived at the club off the back of a simply catastrophic reign at Derby County, which saw the Rams rack up a record low Premier League points total, an unwanted record which still stands.
At Ipswich he had plenty of motivation to get things right, and rebuild his reputation, but 18 months after his appointment, he looks to be taking them backwards not forwards. The owner will have a big decision to make if results do not improve.
Ipswich currently have just five points from five games, an opening to the season which saw them thrashed 6-0 by Blackpool. Their only win came away to fellow strugglers Watford, back on August 21, almost a month ago.
Tonight they host Wolves, a side packed with talent, who will be most people's favourites to snatch a win. So to ask what has gone wrong at Ipswich, for all the talk of ambition when Evans took over, there has been little to no backing in the transfer market.
£8 million was gained for the sale of Connor Wickham to Sunderland, but the club have spent just a minute portion of that on transfers since 2010, which tells its own story.
This summer goalkeeper Scott Loach was signed for £150,000, a shrewd signing, but he is yet to have a real impact. Talented players have been brought in over the past year and a half, Jay Emmanuel-Thomas, Nathan Ellington, and Michael Chopra.
Chopra left promotion chasers Cardiff, so persuaded was he by Ipswich's chances of offering him a better crack at the Premier League, but it has not worked out for either club or player.
The fault of the players must lie partly with themselves, and with the manager too. Jewell has done what he can in the transfer market, with next to no help from Marcus Evans in terms of investment, but on the pitch the boss has failed to get them to gel effectively, and the defence is still shipping goals.
There is a long way to go this season, and it is far too early to start shouting crisis just yet, and a win over Wolves would do them the world of good, but the promised land of the Premier League simply could not be further away.
It was only so long ago Ipswich were enjoying rivals Norwich languishing in League One. Now the Canaries are in the top flight, while it could even soon be Town who head further down the football ladder.
What needs to happen for Ipswich to move forward?
image: © martinrp