Football writer and Ipswich fan Richard Woodall looks back over the last ten years and wonders how they could have been so different. Apart from the sale of Jordan Rhodes, what other ‘what ifs’ could have prevented Ipswich Town from unravelling over the last decade? Here are 20 thoughts for 2020…

(Note: I chose to start this from the beginning of the 2009-10 season and thus ignored Roy Keane’s initial unveiling as boss – something I think we all know was a significant error.…)

• In July 2009, Ipswich boss Roy Keane said the club had lodged a joint £5m bid with Sunderland for striker Daryl Murphy and midfielder Dean Whitehead. How would things have gone if Murphy had been in the team from early on in 2009 as Keane’s Ipswich continued to labour?

• Another example of Town failing to land their targets in the summer of 2009, and this time it was at centre-back. A stellar list of candidates included Celtic captain Stephen MacManus, Sheffield Wednesday’s highly rated Richard Wood, and staggeringly, Sol Campbell, who had walked out on his five-year deal with Notts County just one game in. What if?

• More of a left-field example (no pun intended) is that of Republic of Ireland stalwart Kevin Kilbane who was thought to be considering a loan move to Ipswich to link back up with his old international teammate Keane. In the end, ‘Killer’ Kilbane decided a relegation fight with Premier League Hull was much more enticing. Nothing to do with Keane, of course.

• Brendan Rodgers to Ipswich as Keane’s assistant? Here’s one which has gone under the radar. A year into Keane’s reign, Rodgers had several meetings with Keane at Portman Road to discuss the assistant manager’s role – a job Keane was open about wanting to fill. Back then, the Ulsterman had had mixed spells in charge of Watford and Reading. Where would Town have gone with the often unfairly treated Rodgers helping to steer the mothership?

• Ross McCormack instead of Rory Fallon? Keane wanted a forward, and this was another setback. Ipswich were looking to do business with the Bluebirds and swap Jon Stead for Scotland’s McCormack. The move didn’t happen, and a short while later, Keane, in his wisdom, took League One side Plymouth’s Rory Fallon on loan instead. Failure to complete deals unsurprisingly didn’t go out the window when Keane left…

• Breaking News: Not Roy Keane’s fault.

You only need to say the words ‘Charlie Austin’ and all Blues fans will talk about this being THE example of Town struggling to complete deals. Austin – who had scored 37 goals in 58 starts for Swindon Town - was even ‘in the building’ at Portman Road in January 2011, and about to sign a three-and-a-half-year deal, but in stepped Burnley.  The rest, as they say, is history - with Austin going on to score once every two games over five years, first at Burnley and then at QPR.

• It’s not just concluding deals which was a problem. The summer of 2011 saw two of Town’s key players depart on free transfers. Captain David Norris and defender Gareth McAuley were both offered new deals but chose to leave the club. Norris had been top scorer that season with eleven goals, whilst McAuley was a previous captain. In McAuley’s place, Ipswich put their trust in Ivar Ingirmarsson and Ibrahima Sonko…neither of whom was a success story. Ingirmarsson was ditched six months into his deal after a suspect performance in a 1-3 home defeat to Nottingham Forest, while Sonko was released after one season.

• When Paul Jewell was entering his first full season as boss, the man who had scored eight goals in eight games against the Blues was again linked with a transfer to Portman Road. David Nugent – who had been a target of previous manager Jim Magilton – was said to be keen to leave Portsmouth. As it was, Nugent moved to Leicester. Had Town signed him, he wouldn’t have been able to add another seven to his goal tally against Ipswich…

• Should Connor Wickham have stayed at Ipswich another year? When he was sold to Sunderland in June 2011 for £8m, he became the most expensive player to have moved from the Championship to the Premier League without experience of top-flight football. Having been a regular for Ipswich over the past two seasons, Wickham found appearances hard to come by on Wearside, and the following season, only Michael Chopra reached double digits in finding the net for Ipswich. Wickham ended up going on loan to Sheffield Wednesday the following season. Would a third full season of Championship football have benefited both him and Town?

• The infamous Portsmouth trio: Paul Jewell tried numerous times to bring then Portsmouth midfielder or right-back Joel Ward to Portman Road, with the first time being the January 2012 transfer window. Having had the chance to interview Ward myself a few years ago, he confirmed the deal indeed nearly happen. Jewell – who said the move broke down over personal terms – was also after two other Pompey players. These were centre-back Jason Pearce and goalkeeper Stephen Henderson. Henderson eventually joined Town on loan as a West Ham player.

• A high number of loan players was never Paul Jewell’s intention, the manager said. (In fact, it wasn’t something specific to the Jewell era). But arguably for Jewell, it was the beginning of the end and again prevented Town from building long-term. Halfway through October in 2012, Ipswich had eight loanees: Daryl Murphy, Guirane N’Daw, DJ Campbell, Bilel Mohsni, Massimo Luongo, Richie Wellens, Danny Higginbotham, and Stephen Henderson. This was despite rules saying only five could be in a matchday squad. Jewell insisted that he wanted to sign most of them permanently, but only Murphy eventually did sign. The only other true loanee success was DJ Campbell (who didn’t sign for Town permanently)

• Matt Holland will always remain a popular figure at Portman Road. After Jewell’s infamous DVD review of the Derby game and subsequent ‘mutual consent’ departure, Holland was linked with the role of assistant to Jewell’s successor.  The former Blues captain was said to have been in the director’s box at Portman Road for a game after Jewell’s dismissal. Holland never joined – but think what could have been had he been groomed as McCarthy’s successor? Not only would he have probably been ready for the manager’s job in the future, but he could have discouraged some of Mick’s venomous jibes towards fans as things worsened during his tenure…

• Lost opportunity: Another key juncture in the club’s recent history was the January 2015 transfer window. When December turned to January, Ipswich sat second in the Championship table (47 points from 24 games), a point behind the leaders Bournemouth. Many fans called for the club to invest significantly in the team to add much needed strength in depth. The biggest amount spent was £500,000 for Colchester’s Freddie Sears, who joined along with free agents Noel Hunt and Paddy Kenny. Sears was a success, but could and should have Town gone further in investing at this key time? It meant that Town were reliant on loans later down the line…

• Knockaert to Ipswich? It’s February 2015 and the 13-game run in for Town’s promotion hopes is in the balance. With just 18 outfield first team players fit for the previous game, Big Mick wants to bring in cover for the injured Stephen Hunt. Anthony Knockaert was a key player for Leicester’s promotion charge the previous season, but the Frenchman chose not to drop down a division. Doh!

• The tiniest of margins at Blackburn. If Town had got a draw at Ewood Park on the last day of the regular season, it would have meant a 5th place finish rather than 6th. Should they have beaten Boro over two legs, they could have played Norwich in the PO final – and had a better chance of victory. If only Tyrone Mings’ header had not hit Teddy Bishop and cannoned off to Rudy Gestede for Blackburn’s 3rd goal…

• Stats of 16 goals in just over 60 total appearances isn’t bad for a striker who has yet to reach his peak. Especially if he is a youth product like Jack Marriott. The crunch point for the Ipswich academy graduate (according to McCarthy) seems to have been returning for pre-season overweight; this was enough to see him released at the end of 2014-15 season. Last year, Derby paid Peterborough £3m for his services…

• What if the 5-1 defeat away to Reading hadn’t happened? Mick tried to make Town more expansive but following a nightmare evening in Berkshire, he appeared to reverse this decision. Habits prove hard to break and pragmatic Mick returned as Town’s promising start faded.   

• If Mick was diplomatic…Yes Mick did receive some nasty abuse, but why couldn’t he learn to relate better to his critics? And why was he allowed to get away with lobbing grenades in the direction of Ipswich fans? If Marcus had acted earlier…

• Murphy out and anyone else but Best in? The 2016-17 season was the worst in 58 years for the club. Town went backwards and a large part of that was pinpointed to the selling and then failure to replace Daryl Murphy, so close to transfer deadline day. Leon was the best Town could do as moves for Connor Washington and Marley Watkins failed to materialise.

• If Paul Hurst had had a director of football as he sought to put his mark on the team (still a sore point being felt today), maybe last season wouldn’t have started so disastrously…