James Maddison and Romeo Lavia will be hoping for a lot more success than the majority of the players on this list if, like them, they make the move to a Big Six club immediately after being relegated from the Premier League.
We’ve ranked those that have come before from worst to best…
31) Wayne Routledge (Crystal Palace to Tottenham, 2005)
Spurs paid £2.5m for the then 20-year-old, who played 94 minutes of football for them before a further 295 Premier League appearances elsewhere. It worked for him, but not them.
30) Lee Grant (Stoke to Manchester United, 2018)
He played twice in four years. The first game saw him concede a goal against Derby in the Carabao Cup after Sergio Romero was sent off, then fail to save a penalty in the shootout as they were dumped out. The second saw him concede twice in defeat to FC Astana.
29) Ross Turnbull (Middlesbrough to Chelsea, 2009)
Nineteen starts for Chelsea and 25 goals conceded. Turnbull now works as the Chelsea goalkeeping scout, in a role where he’s presumably tasked with finding far batter goalkeepers than himself.
28) David Bellion (Sunderland to Manchester United, 2003)
Arrived in the same summer as Cristiano Ronaldo and scored a Premier League goal every 229 minutes compared to Ronaldo’s one in every 387 minutes. The ratio imbalance then shifted a bit.
27) Chris Kirkland (Coventry to Liverpool, 2001)
Conceding three goals in six Champions League games isn’t half bad, but he was very much behind Sander Westerveld to start with before Jerzy Dudek came in and immediately usurped them to the No.1 spot.
26) Danny Ings (Burnley to Liverpool, 2015)
“If you could bottle character and spirit, his would sell worldwide,” Jurgen Klopp said in an emotional tribute to the departing Ings after three injury-ravaged seasons at Anfield. You could bottle his knee joint fluid and sell it as laxative.
25) Michael Owen (Newcastle to Manchester United, 2009)
Scored a late winner in a 4-3 win over Man City at Old Trafford and that was about it. Won the Premier League in 2011 in his worst ever goalscoring season up to that point, then went to Stoke.
24) Eddie McGoldrick (Crystal Palace to Arsenal, 1993)
Got three assists in 28 Premier League appearances as the Gunners finished fourth in 1994, before his career rather fell away. There’s a 28-year gap between him and the next player Arsenal signed from a relegated club…
23) Sebastien Bassong (Newcastle to Tottenham, 2009)
“I feel that I have gone backwards, like I have gone from heaven to hell,” Bassong said after playing 28 games under Harry Redknapp in his debut season, before spending the next 30 as an unused substitute.
22) Charlie Adam (Blackpool to Liverpool, 2011)
Just one season at Liverpool, which wasn’t half bad as he claimed nine assists and a couple of goals, before Liverpool realised how utterly mad it was that they had Charlie Adam pulling the strings in midfield.
21) Jermaine Pennant (Birmingham to Liverpool, 2006)
Played a fair bit in his debut season as Liverpool finished third, but never lived up to the huge hype that came when he signed for Arsenal for £2m as a 15-year-old.
20) Ryan Sessegnon (Fulham to Tottenham, 2019)
Big things were expected after his £25m move from Fulham but Jose Mourinho soon put paid to those hopes and dreams. Yet to really get going.
19) Alan Smith (Leeds to Manchester United, 2004)
Koreans using the phrase ‘Leeds days’ (weirdly regularly, by the way) to refer to a person or thing’s heyday tells you everything you need to know about Alan Smith’s time at Manchester United compared to Leeds United, because that is literally what their ‘Leeds days’ phrase refers to. Utterly bizarre.
18) Frederic Kanoute (West Ham to Tottenham, 2003)
Only truly appreciated having left the Premier League, as he banged in 135 goals for Sevilla, his time at Spurs was the least successful of his career.
17) Scott Parker (West Ham to Tottenham, 2011)
Won the Football Writers’ Player of the Year to earn his move to Spurs, which tells you just how sh*t the rest of the West Ham team was as they finished rock bottom. Played next to Luka Modric in his first season but was forced out by Mousa Dembele in his second.
16) Darren Bent (Charlton to Tottenham, 2007)
Joined quite the striker cast at Spurs with Robbie Keane, Jermain Defoe and Dimitar Berbatov. Scored 25 in 79 games but had further chances Harry Redknapp’s “missus” could have scored.
15) Adam Johnson (Middlesbrough to Manchester City, 2009)
Scored some goals. Got some assists.
14) Xherdan Shaqiri (Stoke to Liverpool, 2018)
Barely played in truth but the guy’s won the Premier League and Champions League, and has ludicrous calves.
13) Glen Johnson (West Ham to Chelsea, 2003)
Now the purveyor of bizarre opinions (cheers, mate), Johnson signed for Chelsea in that incredible first transfer window under Roman Abramovich and won two Premier League titles, mainly as understudy to Paulo Ferreira and Geremi.
12) Peter Crouch (Southampton to Liverpool, 2005)
Quite the pressure on Crouch to join Liverpool immediately following the Miracle of Istanbul after he himself had only been in the Southampton team for about six months. It took him four months to score his first goal, but he managed a further 41 in four seasons with the Reds.
11) Paul Robinson (Leeds to Tottenham, 2004)
Remembered for a few England howlers but you’ve got to be alright to get 41 caps, and he was better than alright for Tottenham.
10) Kieran Trippier (Burnley to Tottenham, 2015)
Had to bide his time before Kyle Walker left for Manchester City, but was very good for a while with Danny Rose on the opposite flank. He’s since become much, much better.
9) Nathan Ake (Bournemouth to Manchester City, 2020)
£40m seemed like a lot and still did until about six months ago, when Pep Guardiola made us all look like fools by revealing Ake’s actually a left-back.
8) Aaron Ramsdale (Sheffield United to Arsenal, 2021)
He’s still got a rick in him but it’s fair to say we’ve all got egg on our faces for chortling at his £25m transfer fee. Absolute snip.
7) Moussa Sissoko (Newcastle to Tottenham, 2016)
Looked like a weird and very average signing before he became an absolute monster for Spurs in their run to the Champions League final.
6) Jermain Defoe (West Ham to Tottenham, 2003)
One-hundred-and-forty-three of his 305 career goals came for Spurs at an average of one every 160 minutes. Brilliant striker.
5) Stephane Henchoz (Blackburn to Liverpool, 1999)
Played alongside Sami Hyypia so Stephane arguably wasn’t the head Henchoz at the time, but they formed a dominant partnership for Liverpool, conceding just 30 goals in the 2001/02 Premier League season.
4) Georginio Wijnaldum (Newcastle to Liverpool, 2016)
In search of a whole new midfield Liverpool would do well to find another Wijnaldum, who had that ability of not looking as though he did an awful lot because he was doing little bits of everything all the time.
3) Joe Cole (West Ham to Chelsea, 2003)
Three Premier League titles, three FA Cups and two League Cups in seven years at Chelsea. His dancing feet to score against Manchester United to claim the Blues’ second title under Mourinho was the moment of many.
2) Andy Robertson (Hull City to Liverpool, 2017)
£8m he cost them. That’s £1m per goal (not sure why we brought that up), and £127k per assist (actually even that doesn’t sound that great). He was very f***ing cheap and is very f***ing good, alright?
1) Roy Keane (Nottingham Forest to Manchester United, 1993)
Sigh. He only just squeezed in as well. Forest were relegated after the very first Premier League season and Roy Keane upped sticks for United because he’s got no loyalty, or something. He then won seven Premier League titles, four FA Cups and the Champions League, captaining them for most of it. He was very good.