Millwall 1988-89: Who let the Lions out?
- Graham Dunn
- Nov 14, 2024
- 7 min read
Updated: Dec 3, 2025
For many, Millwall 1988–89 First Division feels like a forgotten chapter — a brief, brilliant moment when the Lions roared among England’s elite. John Docherty’s unfancied side, built around the prolific partnership of Tony Cascarino and Teddy Sheringham, defied all odds to top the table and shake up the old order. For two unforgettable seasons, Millwall brought grit, goals, and glory to The Den.
I have a blind spot when it comes to Millwall. In my mind the Lions have mostly plied their trade in the top two divisions, aside from a blip in the third tier a few years back.
The reality is different. Spectacularly so.
Yes, Millwall have spent a majority of the last 40 years at Championship-level. But they also spent 14 of them skulking around the third tier.
The blip, it turns out, was the two years they spent from 1988 to 1990 in the top-tier.
That is not just a blip of my football lifetime. Those two seasons are the only years Millwall have ever been in the top-flight.
Closer scrutiny shows that Millwall, in fact, are one of the least top-flight sides of all. Statistically they have spent 2% of their football seasons in the top division. That is lower than all but five of the other 65 English league clubs to have ever graced the first division in all its iterations. And one of those is Swindon.
It goes some way to explaining why Millwall making it into the First Division was so special and unlikely – and for visitors to the Lion’s Den, for one season at least, so unwelcome.
Neither was there much sign that this history was about to be made. George Graham had taken Millwall up to what was then the Second Division in 1985, only to attract Arsenal’s attentions.
The subsequent appointment of John Docherty hardly set pulses racing - though perhaps gave some hint of what was to come. His five-year stint in charge at Cambridge United had begun by taking them up to the second tier for the first time in their history. But it ended in 1983 during what became a then-record 31 games without victory.
Docherty had since been assistant manager at Brentford to Frank Mclintock – who later returned the favour to become Docherty’s assistant at Millwall. The club ended the 1986-87 season, his first in charge, looking mostly over its shoulder in 16th place.
However, chairman Reg Burr rolled the dice, bringing in George Lawrence from Southampton and Kevin O’Callaghan from Escape to Victory to provide supply down the wings (O’Callaghan having given up the gloves after losing his place in nets to Sylvester Stallone).
Most significantly, he brought in Tony Cascarino from Gillingham for a then not insignificant £225k.
This was to be the start of golden partnership with Teddy Sheringham, who had enjoyed a breakthrough with Millwall the previous year.
Key facts
2% - amount of time spent in top tier throughout club history;
10 – home wins in debut First Division season, topped only by Liverpool;
99 – goals, shared almost equally, between Cascarino and Sheringham over a near three season partnership;
Sheringham would score 24 goals and Cascarino 23 in a side in which timed its run perfectly. Having not featured in the top two all season, Millwall won seven games in a row to win promotion as champions at Hull with a game to spare.
The late charge caught everyone out, not least the PFA Division Two team of the year – which in another sign of how unfancied Millwall were, featured none of its players (an omission explained either by the song being true and no-one liking them or postal votes meaning nobody voted for players from a team lying in 7th in February).
While not including at least one of Cascarino or Sheringham seems bizarre, the wider omission of Millwall players is perhaps unsurprising given their general lack of stars. The team was built on hard work and hard men – none harder than midfield warrior Terry Hurlock – and ‘journeymen’ pros like Keith Stephens and Alan McLeary at the back.
Only Lawrence and O’Callaghan had previous top-flight experience, and aside from the addition of QPR left back Ian Dawes, it was essentially the same squad that Millwall took into the First Division.
There was little reason then to think that Millwall would do anything other than make up the numbers. Yet, they were on a roll and incredibly lost only one of their first 13 top-flight games ever.
They topped the table at the start October, ended 1988 in third place – and were back in third for most of March. Millwall would have been dreaming of a place in Europe, were it not for the ban on English clubs competing in European competitions at the time.
Millwall were direct and committed. Les Briley and Hurlock in the middle were a combative pairing (while the latter’s three England B caps that season show there was more to his game than being a hard man, Graeme Souness later signing him for Rangers underlines he did like a tackle).
Their wide players thrived, particularly O’Callaghan and later Jimmy Carter, delivering for the prolific front two. Cascarino and Sheringham took up where they left off, between them scoring 14 goals in Millwall’s first nine league games. They would end the season with 15 goals apiece.
Millwall’s success was built on their home form. Millwall won 10 of their first 14 games at the Den, proving equally intimidating to visiting players and fans alike. They only lost their first home game in December to West Ham - one of eight London teams in the top-flight that year.
A record nine London teams, including Millwall, featured in the top tier in the 1989-90 season.
However, a two-nil home win against Aston Villa on 18 March was to prove Millwall’s last win, either home or away, as they fell away to 10th after failing to win any of their last 10 league games – a worrying sign of what was to follow.
Despite a bright start in which Millwall won four of their first seven games the following season - briefly topping the table once again - another two-nil victory against Aston Villa in mid-December was to be the Lion’s only other league win that season. Millwall spent the second half of the season in the relegation zone and ended the year cut adrift at the bottom.
By that point the band was already breaking up. The influential O’Callaghan was injured, Docherty and Mclintock were sacked in February, and Cascarino sold to Aston Villa for £1.1 million in March.
Cascarino’s sale ended his partnership with Sheringham, which was not just one of the most prolific, but also surely one of the most equitable in history. Eschewing the little man playing off a big guy model, both could play as a target man and continued to match each other’s goal returns by scoring 11 each in 1989-90 before Cascarino’s sale (Sheringham ended the season with 12). Across their nearly three-season partnership, their 99 goals were all but shared – Sheringham scoring 50 to Cascarino’s 49.
Sheringham was to go on to strike equally profitable partnerships with the likes of Alan Shearer for England and Andy Cole for Man United (if not as friendly), by which time he had refined his reputation as much as a creator as a goal-scorer. That though was not before he had rounded off his Millwall career with a staggering 37 goals (including four hat-tricks) as Millwall under Bruce Rioch just missed out on an immediate return to the top-tier in 1990-91.
Sheringham signed off after 111 goals, a club record until overhauled by Neil Harris, and was sold to Nottingham Forest that summer for £2 million. That marked the end of an era. Briley moved on that summer too, while Hurlock had left for Rangers the previous year – though did return for a 13-game cameo in Millwall’s 1994 play-off making side, marking his return in style by getting sent off nine minutes into his second home debut.
Injury, which had deprived Millwall of O’Callaghan during their relegation season, all but ended his career, while another bright spark on the wing Carter was sold in early 1991 to begin a five-year odyssey on the fringes of Liverpool and Arsenal.
Since then, and other than a 2001-02 play-off appearance under Mark McGhee, Millwall have seldom threatened to repeat history and remain very much, not a top tier side.
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How we ranked them
We have five categories of greatness from our five-star All-Time Greats category at the top to our one-star Blinkered Greats category at the bottom. While short-lived, Millwall’s moment in the sun bringing with it the incredible Cascarino-Sheringham partnership and Terry Hurlock’s hair, tipped them into our two-star category.
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Edge of Greatness
Listen to the full podcast:
Join hosts Graham Dunn and Jamie Rooney — with Fulham fan and London football expert Stuart Burgess — as they relive Millwall 1988–1990, the Lions’ remarkable rise, Cascarino–Sheringham’s brilliance, and Terry Hurlock’s unforgettable bite.
Take your pick. George Lawrence is Oxford royalty for his performances under Jim Smith; Steve Anthrobus and Steve Wood less so. But Jimmy Carter perhaps deserves more credit than he gets for an exceptional first loan spell at the club, even if a subsequent less effective one followed. A crueller person might point out Oxford, a team with only more season in the top tier than Millwall, were one of the relegated teams the Lions replaced in 1988.
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