Phew! What a task! Trying to assess the good, the bad and the downright dreadful of Town’s managers certainly wasn’t simple!

I’m sure you won’t agree with some of my views, or my rankings, but hopefully it will give you some food for thought and bring back some memories - some good, some awful!

In all, Ipswich have had 19 managers, but I have excluded two - the first boss, Mick Burns, who oversaw a pre-war Southern League side, and also the current manager, Kieran McKenna, because I felt it was impossible to give him a placing. Hopefully he will eventually end up somewhere near the top of the managerial league table!

So, here they are, ranked from 17th to 1st, starting with the very worst.

17th - and last by some distance! Paul Hurst

An unmitigated disaster. Appointed after Mick McCarthy’s ultimately acrimonious departure, Hurst was supposedly the new broom Ipswich so desperately needed.

Instead, after just one win in 15 league games, Hurst was on his bike and Town were plummeting towards the third tier for the first time since the 1950s.

Hurst brought in a load of lower league players, put them together - and got distinctly lower league performances.

The alarm bells started ringing as early as August, when Ipswich were dumped out of the League Cup on penalties by mighty Exeter. Now, Hurst certainly isn’t the only recent Town boss to be humiliated in cup competitions - in fact, for more than a decade now, it’s become a habit.

The difference with Hurst at Exeter was that he absolutely tore into the players in an after-match interview, basically accusing them of not trying. It was the beginning of the end.

16th Jackie Milburn

“Wor Jackie” was a goalscoring legend with Newcastle, but undoubtedly a managerial flop at Portman Road.

He was really on a hiding to nothing, inheriting Alf Ramsey’s ageing, fading team which had stunned the football world two seasons earlier by winning the league championship at the first attempt.

As Ramsey moved to the England job, Milburn was left with a pretty hopeless task.

Goalscoring talisman Ray Crawford left for Wolves, and stalwarts like Roy Bailey, Ted Phillips, John Elsworthy and Jimmy Leadbetter were past their best.

Milburn shopped in Scotland for replacements, but the likes of Joe Davin and John Colrain weren’t really up to the task and Ipswich were relegated at the end of Milburn’s only full season. He was put out of his misery almost immediately.

Those who met Milburn said he was far too nice to be a top manager, lacking the necessary ruthless streak.

15th Paul Lambert

The former Norwich and Colchester boss took over from the disastrously unsuccessful Paul Hurst in the autumn of 2018, and oversaw one of the strangest periods in Ipswich Town’s history.

Despite a disastrous start under Hurst, Ipswich were by no means doomed to relegation when Lambert arrived.

Results improved only marginally, but no-one seemed to notice. Lambert became known as “PR Paul” as he wooed the fans and his popularity soared even further when he got involved in a bench bust-up on his return to Carrow Road.

Bizarrely, Portman Road was buzzing as relegation was confirmed with fans convinced the team would storm their way back to the Championship.

Despite starting the next two seasons like a house on fire, the team faded badly to finish mid-table both times.

Lambert’s press interviews became increasingly tetchy and strange, and by the end he was looking and sounding a broken man.

He clearly wasn’t helped by then owner Marcus Evans’s lack of investment, but there’s no doubt Lambert massively under achieved at Ipswich.

14th Paul Cook

Another Paul, another nightmare... Cook arrived as the self-styled “Demolition Man,” on a mission to clear out the underperforming squad he inherited from Lambert.

Well, he certainly managed to transform the personnel. It was a case of fast-moving revolving doors as the vast majority of the squad left, to be replaced by no fewer than 19 new players.

If ever there was a case of too much change too quickly, this was it. The new players performed like a bunch of strangers - which they were - and “needing time to gel” became the most used phrase among Town supporters.

Meanwhile, Cook’s former assistant Leam Richardson was impressing at Wigan, who ultimately won promotion.

Town got off to a poor start, and as the days became colder, there was no real sign of improvement, and Cook paid the price. Subsequently, his managerial career has continued on a downward spiral.

Just one thing saved him from an even more ignominious placing - he did sign Wes Burns, George Edmundson, Christian Walton, and Sam Morsy, all players we hope will be part of a promotion-winning team next season,

13th Paul Jewell

One of several unsuccessful appointments by Marcus Evans. On the day Jewell arrived at Portman Road, Evans explained to me how he’d done his homework on the new boss, and had been particularly impressed by his track record of winning promotions.

It didn’t work out, though, and by the time Jewell left in the autumn of the following year, Town were staring down the barrel of a relegation battle to preserve their place in the Championship.

His departure was memorably farcical - it could only happen in football. After a particularly dismal home defeat to Derby, Jewell failed to show for his customary post-match media duties.

When his assistant Chris Hutchings was asked where the gaffer was, he replied: “He’s watching a video of the game.” Jewell was out of the door the following day.

12th Roy Keane

I still remember how excited I was when Keane was appointed Ipswich manager. He was, after all, an absolutely legendary figure who had been an utter colossus as Man Utd captain. Playing and managing are two very different things, though...

Despite healthy investment from owner Evans - Keane was his first managerial appointment - the first season under his management saw Town fail to win any of the first 14 league games and finish a monumentally disappointing 15th.

It wasn’t long before tales of dressing room fall-outs started emerging, results didn’t improve, and Keane was on his way halfway through his second season.

Despite being a flop as manager, what Keane did bring was massive media attention. Never one to duck a question, his press conferences were regular headline-grabbers. I vividly recall some comments he made about Wayne Rooney which made the “bongs” at the start of News at Ten!

Anyway, he’s a top TV pundit now, and apparently regards coming to Ipswich as one of his biggest mistakes. Love you too, Roy!

11th John Duncan

Affable Scot, Duncan, presided over one of the dullest periods in the club’s history but, given the context, and what’s happened more recently, he actually did ok.

Duncan took over from Bobby Ferguson after Town had narrowly failed to bounce back to the First Division at the first attempt.

In his two seasons, the team finished in the top half of the Second Division both times, but failed to make the fledging play-offs. It’s important to remember that expectations were rather higher back then - this is only a few years after the end of the Robson era. Hence Duncan’s time is pretty harshly judged.

His most memorable feat was signing Sergei Baltacha. The USSR defender arrived amid much fanfare - the Evening Star welcomed him with a front page banner headline in Russian.

Now, Baltacha had played 45 times for the USSR as a sweeper, so clearly was no mug. But where did Duncan play him? Either on the right-hand side of midfield, or in a traditional back four. Very strange.

10th Jim Magilton

A hot topic, this one. Was Jim unfairly and prematurely hounded out of the club thanks to a campaign orchestrated by the evil then editor of the EADT? (that’ll be me then...)

Or was he failing to deliver, given the squad at his disposal, and his era should be viewed as one of under achievement? You pays your money, you takes your choice! Given the history, no great surprise that I am firmly in the latter camp. Look at the facts - finishes of 14th, 8th and 9th in the Championship don’t exactly get the pulse racing, do they?

But, of course, I realise it’s not as simple as that. Firstly, Jim was massively important and popular as a player - arguably the most crucial signing in the Burley era, and ultimately one of the heroes of Wembley 2000.

The football we played under Jim was often exciting. He also delivered our most recent victory over Norwich - ironically, he was sacked 24 hours later. Finally, he brought Gio dos Santos to Portman Road - surely our best player since the Robson days.

9th Bobby Ferguson

Poor old Fergie. He really was on a hiding to nothing. Taking over from Bobby Robson just as the great side of the early 1980s was breaking up was always going to end in tears.

Ferguson spent most of his time as manager waving goodbye to departing superstars and, with no money available, trying to replace them with kids or bargain basement buys.

Within a short space of time, we were watching Mich D’Avray and an ageing Alan Sunderland instead of Paul Mariner and Alan Brazil, and Trevor Putney instead of Frans Thijssen.

Given the circumstances, Ferguson did quite well. He kept us in the First Division for a season or two longer than we really should have, and got us into the play-offs in our first season back in the Second Division.

Fergie fans insist he was the tactical genius during the Robson glory years, including the master stroke of playing striker David Geddis on the right wing in the 1978 FA Cup Final, giving Sammy Nelson an absolute nightmare and setting up Roger Osborne’s winner.

8th Mick McCarthy

Another real Marmite manager who definitely polarises opinions among supporters. One thing is certain - he saved us from relegation and successfully stabilised the club when he took over from the disastrous Paul Jewell.

Still on the plus side, he gave us a memorable season in 2014-15 when his Daryl Murphy-inspired side made it to the Championship play-offs. If only he’d managed to persuade Marcus Evans to spend more in the January transfer window...

But, as we all recall, it turned sour. The purse strings tightened, and life became a grim, dour battle to finish mid-table in the Championship.

The football was terrible to watch, fans became restless, Mick got grumpy with them, and the rot really set in. He began to say daft things like suggesting the more supporters called for exciting loanee Bersant Celina to come off the bench, the less likely he was to do it. Excuse me?

Then we had the extraordinary gesture towards Ipswich fans when Luke Chambers scored what we thought was a late winner at Norwich. There really was no coming back from that.

There are those who say if we’d kept McCarthy, we’d still be in the Championship. Maybe. But who would be watching - one man and a dog?

7th Joe Royle

Genial, ever-smiling Joe did a terrific job. To reach two play-offs in the aftermath of the club going into administration really was an awesome achievement.

Joe apparently believed that another £1 million in the transfer kitty would have seen him take the club back to the Premier League. He was probably right, but that kind of money was never going to be available given the circumstances.

Royle’s football was an utter joy to watch. I still smile at the memories of Shefki Kuqi, a young Darren Bent and Tommy Miller terrorising Championship defences. I felt so sorry for Royle when all three left in one summer - having scored no fewer than 55 goals between them in the previous season.

Royle left on good terms with chairman David Sheepshanks, and surely every Town fan will look back at his time with the club with really happy, fun memories.

6th John Lyall

His achievement in taking Ipswich back into the top-flight in 1992 - and keeping them there for a couple of seasons - should not obscure the unfortunate last months of his time at Portman Road.

Lyall come to Ipswich as a West Ham legend, having taken the London club to their highest league finish and an FA Cup triumph in 1980, thanks to Trevor Brooking’s header.

In his second season at Ipswich, his workmanlike team won the Second Division championship, to join the new Premier League in its inaugural season. Town started the next two seasons very strongly but then faded badly, only surviving by the skin of their teeth on the last day of the 1993-94 season.

John moved upstairs, leaving Mick McGiven in charge of the first team. It was a disaster, fans protested on the pitch, and Lyall resigned in December 1994, leaving the way open for George Burley.

5th Bill McGarry

There might be some eyebrows raised that McGarry ranks so highly in this list. After all, he doesn’t feature regularly in discussions about Town’s glorious history.

But let’s put his achievements in context. He inherited a club in a big mess when he took over from Jackie Milburn in 1964.

Tough guy McGarry sorted out the mess, stabilised the club, and then began to rebuild the team. Crucially, he brought Ray Crawford back and the returning goalscoring hero played a big part in the 1967-68 Division Two title triumph.

He also gave debuts to future stars like Mick Mills and Colin Viljoen, for which Bobby Robson would be very grateful!

McGarry’s departure for Wolves was rather sour. He described the Molineux outfit as a “bigger club” - which proved to be far from the case during the subsequent decade!

4th Scott Duncan

Another whose presence in the higher echelons of Ipswich Town managers might surprise a few people. But his achievements at Portman Road were very significant and, in many ways, created the club we know today.

When Duncan arrived at Ipswich as the Second World War was looming, the club was in the Southern League.

Under his leadership, Ipswich joined the Football League for the first time, and became established as a league club, albeit in lowly Third Division (South).

In the 1953-54 season, the team won its first professional honour, capturing the Third Division (South) title, giving them the chance to sample Division Two football for the first time.

Although they were immediately relegated back to the third tier, Duncan had created a professional football club and a platform on which the incoming Alf Ramsey could build.

After Ramsey’s arrival, Duncan stayed on for three more seasons as club secretary, giving 18 years service in total. An important and often underestimated figure in the history of the club.

3rd George Burley

To finish on the podium behind the two managerial knights, Ramsey and Robson, is some achievement for Ipswich Town legend George Burley.

The Scottish international full-back had already played 500 games for Ipswich when he returned to Portman Road as manager over Christmas 1994.

By then, the team was already pretty much doomed to relegation from the Premier League, and Burley had to suffer the indignity of the record 9-0 defeat at Man Utd on the way to the inevitable. Back in the second tier, Burley got to work and the next few years were characterised by constant progress, some cracking football - and heartbreaking play-off defeats.

Burley combined emerging youngsters like Kieron Dyer, Richard Wright and James Scowcroft with experienced signings such as Jim Magilton, David Johnson and, ultimately, Marcus Stewart to build an irresistible team.

Eventually, it all came right in the play-offs in 2000, with memorable games against Bolton in the semis and Barnsley in the final at Wembley. Those games remain my favourite Town moments - and I was at the FA Cup and UEFA Cup finals!

It got better still...Burley’s team amazed the footballing world by storming to fifth place in the Premier League, qualifying for the UEFA Cup and only missing out on the Champions League on the last day of the season. Burley deservedly won Manager of the Year.

After that, it went wrong. Some unwise signings - notably Matteo Sereni and Finidi George - didn’t work, and seemed to upset the balance of the team.

Ipswich were relegated and eventually, after a humiliating defeat at Grimsby, Burley was sacked. It was an awful but inevitable moment. I remember a very upset David Sheepshanks calling me to say how much he hated doing it. But that sad ending will never detract from George Burley’s monumental achievements. A true Ipswich great.

2nd Sir Alf Ramsey

The toughest, tightest call of all. Ramsey or Robson, which is better? I know one thing - there are many, many football clubs who would love to be able to have this argument. In the end, I have placed Ramsey second. There are many supporters - mostly those who really remember his triumphs - who would disagree, and insist he should be at the very top of the pedestal.

It’s true that his contribution to the development of the club was phenomenal. He took a mediocre third division team and, within only a few years, had transformed them into the most unlikely of league champions. I believe it still ranks as the biggest shock in English football history.

The story is well documented, of course. Ramsey took a bunch of no-hopers, has-beens, and promising kids and used his tactical genius to ambush the cream of English football.

At Ipswich, he created the prototype of the “wingless wonders” England team who, just four years later, won the World Cup on that iconic afternoon at Wembley Stadium.

I’m sure I’m not the only football fan who finds Ramsey an enigma. His public persona was austere, to say the least, and he was extremely awkward in TV interviews. I still smile at the memory of the gushing BBC interviewer shoving a microphone in Ramsey’s face immediately after the league championship triumph. When he had finally finished telling Ramsey how wonderful he thought he was, he asked him how he felt. “I feel fine,” was Ramsey’s response.

Ramsey lived in Ipswich from the mid-1950s until his death in 1999, but you would hardly have known we had England’s greatest football manager in our midst. He preferred a low profile, playing golf at Rushmere once a week with some close friends. Yet, to his players, this publicly awkward man was an inspirational hero. If you talk to Ray Crawford, you get a sense of the high esteem in which the players held their boss.

It‘s very powerful, and helps to explain Ramsey’s incredible success with both Ipswich and ultimately England.

1st Sir Bobby Robson

Who else? The extraordinary man who made impossible dreams come true for Ipswich Town fans like me. For the best part of a decade under Robson, Ipswich were not only one of the best teams in England, but across the whole of Europe.

As everyone knows, we won the FA Cup and the UEFA Cup, and came agonisingly close to capturing the First Division title.

There were seemingly endless European campaigns, visits from giants like Real Madrid and Barcelona, virtually a whole team of internationals, And widespread admiration and acclaim for Robson, his team, and the club as a whole. We all thought it would never end...

But, we must never forget, the early days were very different. Robson arrived early in 1969 as the Town board’s third choice, to inherit a team struggling to establish itself in the top division.

The first few seasons were a real struggle, with poor results and some players not taking kindly to their new, young manager. Infamously, there was a physical fight with veteran players Bill Baxter and Tommy Carroll as Robson battled to assert his authority.

A major turning point came in September 1971 - almost three years after Robson arrived - when sections of the Portman Road crowd called for his head as a George Best-inspired Man Utd demolished Ipswich.

Chairman John Cobbold stood by his man, Robson bought Allan Hunter and the rest, as they say, is history.

Amazingly, Robson bought barely more than a player a season during his 13 years at Ipswich. Mind you, they were good ones, including the Dutch duo Arnold Muhren and Frans Thijssen, and striker Paul Mariner.

The rest of his teams were homegrown superstars - the likes of Mick Mills, Kevin Beattie, George Burley, Alan Brazil, Brian Talbot and Eric Gates. Wonderful players, all of them.

Sir Bobby, of course, went on to great things with England.

At Ipswich, he gave us our very best, most memorable days. For that, he will always be an absolute hero. And that’s why he is our greatest manager.