Ipswich Town have endured another challenging campaign in League One and they will be facing a major rebuild over the summer as Paul Cook looks to make some much-needed changes.

The Tractor Boys have not been able to achieve their goal of securing promotion back to the Championship in the last two seasons now. Paul Lambert’s departure and the departures of a lot of the players who have been in and around the squad the last few years signal a change in direction.

It has been a difficult period for the club over the last 20 years, and that has seen them drop down from the Premier League at the start of the period down to the third tier. However, there have still been a number of good English players that have been part of their side in that time.

With that in mind, we have had a go at creating a list of their top 10 best English players from the last 20 years. As you can imagine it was a difficult task, but see if you agree with our list and order here…

Before kicking off this list, it is worth noting that there were a number of players that were considered and very nearly selected in this list. Those include the likes of Jermaine Wright, Connor Whickham, Martyn Waghorn, Matt Richards, Tyrone Mings, Danny Haynes, Marcus Bent, and Grant Leadbitter amongst others.

However, starting off the list is Kelvin Davis who is the only goalkeeper to make the list and deserves his place here for the performances he was able to produce as Ipswich’s number one between 2003 and 2005. The keeper arrived at Portman Road on a free transfer and proved to be a bargain making 45 appearances in his first campaign as they finished in 5th place but lost in the play-offs.

The following year, Davis was in fine form once again and helped the Tractor Boys reach the play-offs for a second successive campaign. However, they were once again beaten at the semi-final stage this time by eventual winners West Ham. The keeper though was named in the league’s Team of the Year and he was snapped up by Sunderland that summer.

Coming in next in the list is midfielder Cole Skuse, who makes the list having managed to be an excellent servant for the Tractor Boys throughout his eight-season stay with the club. He might not have had the quality of some of the players to miss out on the list, but he always gave his all and that is why we had to include him here.

Skuse was signed by Ipswich in the summer of 2013 from Bristol City and he instantly became one of their most important players in the middle of the park making 43 appearances in the league and helping them to a 9th place finish. The following campaign, he played a major role in the Tractor Boys making it into the play-offs making 40 league appearances and scoring one goal in the process.

The midfielder continued to be a vital part of the side under Mick McCarthy for the next three campaigns, but he was not able to help them reach the top-six again in that period. Following Paul Hurst’s arrival as manager, Skuse remained a key player but could not help keep the club in the Championship even after Paul Lambert had taken over.

Last term, Skuse remained a key player in the third tier and he managed to make 29 appearances in League One but injuries have limited his impact this term and he will leave the club in the summer after making well over 270 appearances.

Next in the list is midfielder Tommy Miller, who makes it into the list because of the form he displayed during his two separate spells for the Tractor Boys during the last 20 years. That saw him make well over 200 appearances for the club.

Miller was signed by Ipswich in the summer of 2001 after he had enjoyed an excellent season with Hartlepool United firing in 20 goals in all competitions. He did not manage to fully establish himself in the team in his first season as they were relegated from the top-flight. However, he showed his worth the next season registering six league goals in 30 appearances, before reaching double figures with 11 goals in all competitions the following campaign.

The midfielder enjoyed an impressive 2004/05 campaign for Ipswich and he managed to weigh in with 15 goals in all competitions to help the Tractor Boys make it into the play-offs. However, after they were beaten in the semi-finals by West Ham, he left on a free transfer to Sunderland.

He returned for a second spell in the summer of 2007 and went on to score a further 11 goals for the club across the next two campaigns before departing once again for Sheffield Wednesday.

Another player who makes the list due to the level of service he gave the Tractor Boys during his lengthy spell with the club is the versatile Richard Naylor. He managed to make over 370 appearances for the club, and although some of those were outside of the last 20 years, he enjoyed most of his time with Ipswich during this period.

Naylor was more of a bit-part player under George Burley at the start of the 2000s in the top-flight but he still contributed when he was given the chance to feature. It was not until they were relegated that he came back into the fold as a key player. He did also play a major role in their challenges for promotion in both the 2003/04 and 2004/05 seasons.

He continued to be a key part of the squad during the next four campaigns and he was handed a testimonial in September 2006. He also helped to provide cover in multiple positions and during the 2008/09 campaign, he was handed the captaincy. That proved to be his final year with the Tractor Boys and he left for Leeds United in 2009.

Making it into the list here is midfielder Ian Westlake, who was a strong performer for the Tractor Boys during his time at the club and managed to make well over 120 appearances for them during his time in the first-team at Portman Road.

Westlake progressed through Ipswich’s youth team and was given his breakthrough for the Tractor Boys during the 2002/03 campaign. However, he did not become a regular in the side until the following season. In 2003/04 he was one of their best performers and fired in seven goals in all competitions as they reached the Championship play-offs and was named their Player of the Year.

The following season, Westlake continued his fine form for Ipswich and he managed to score eight goals in his 50 appearances in all competitions and again featured for them in the play-offs only for them to lose to West Ham in the semi-finals. Injuries limited his involvement in the 2005/06 campaign and at the end of the season, he moved to Leeds United.

Coming into the list here is defender Aaron Cresswell, who is fully deserving of his place here for being one of the finest left-backs the Tractor Boys have had in the last 20 years. While he has also gone on to prove himself to be a quality Premier League performer since leaving the club.

Cresswell was signed by Ipswich from Tranmere Rovers in the summer of 2011, and he proved to be an excellent addition to the squad making 46 appearances and being named as the club’s Player of the Year thanks to a string of impressive displays. The following campaign, the left-back continued to showcase his potential and he also added four goals, one of which won the club’s Goal of the Season.

The 2013/14 campaign proved to be Cresswell’s last at Portman Road and the defender was once again in excellent form throughout the campaign. He managed to earn himself a place in the division’s Team of the Year as he helped the Tractor Boys secure a ninth-place finish. However, the following summer he was sold to West Ham for well over £3 million.

Arguably the best English centre-back that the Tractor Boys have had in the last 20 years in terms of ability and impact on the side is John McGreal. He managed to make around 150 appearances for the Tractor Boys in his five-season stay with the club.

McGreal was signed by Ipswich by Burley in the summer of 1999, and so his first season where he played a key role in helping them clinch promotion to the top-flight is outside of the period we are looking at here. However, the following year in the Premiership, he played a vital part in helping the Tractor Boys secure a fifth-place finish and qualify for the UEFA Cup.

However, the following year he could do little to prevent them from being relegated from the top-flight despite delivering some good performances and making 33 appearances. His final two years with the club were impacted by injury.

He still played a crucial role in them reaching the play-offs in the 2003/04 campaign before he left the club in search of a longer contract offer the following summer.

One of the best English forwards that Ipswich have had in the last 20 years is Marcus Stewart. He managed to produce arguably one of the finest seasons of form out of anyone in that period during the 2000/01 campaign in the Premier League.

Stewart had managed to play a pivotal role in getting Ipswich into the Premier League during the 1999/2000 season, which is just outside of the period we are concerned with here. However, he continued that form into the Tractor Boys’ first campaign back at the top table and was the second top scorer in the league and the highest English scorer with 19 goals.

That form helped Ipswich secure an impressive 5th placed finish. The following year though he was not able to help them stay in the top-flight but his six goals was still enough for him to earn the club’s Player of the Year award. Stewart was snapped up by Sunderland following their relegation, but he was a joy to watch at times during his spell at Portman Road.

One player that had to make this list is defender Luke Chambers, who has been a magnificent servant for the club ever since he arrived from Nottingham Forest. He is the only player on this list to feature in their list of top ten appearance makers in their history.

Chambers has spent nine seasons with the Tractor Boys and he has been pretty much a key player in every single one of those campaigns never making less than 30 league appearances. His performances in the 2014/15 season, in particular, stood out and were a vital part of the reason why they were able to reach the play-off semi-finals under McCarthy.

Despite ultimately being part of the squad that were relegated to League One in 2018/19, Chambers’ reputation should be untarnished. He has still been a key player for them with his leadership qualities in the third tier in the last two campaigns.

It is sad that Chambers’ lengthy spell with the club is coming to an end this summer. However, he has to go down as one of their finest servants in the last 20 years and given his appearance record will always be highly regarded around Portman Road.

Rounding off the list is another player who it would have been impossible not to include. Darren Bent was an excellent scorer for Ipswich during his time at Portman Road and went on to become an England international and a reliable Premier League scorer after he left the club.

Bent progressed through Ipswich’s academy and he managed to sign his first professional deal in the summer of 2001. He went on to make five league appearances during their 2001/02 campaign as the club were relegated from the top-flight. He announced his arrival the following year firing in 18 goals in all competitions and being named the club’s Young Player of the Year.

The forward was then a vital part of the Tractor Boys’ push for promotion via the play-offs in the 2003/04 season with him netting 15 league goals and 16 in all competitions. His partnership with Shefki Kuqi flourished the following year and he hit 20 goals for the season as he helped them reach the play-offs for the second successive campaign.

Following Ipswich’s defeat by West Ham in the play-offs, Charlton made a move for Bent in the summer of 2005. It proved to be an astute signing for the Addicks and he was a very reliable scorer in the top-flight for the likes of Tottenham, Sunderland and Aston Villa after that.