There was a brief period, about eighteen years ago now, when Bristol Rovers were one of the best attacking teams in the country. This might be hard to believe for anybody living outside of BS7, but it was true, at least to my doughy sixteen-year-old eyes.

Overseeing the Rovers in their final season of the millennium was Ian Holloway, three years into the first posting of what would become a nomadic managerial existence within the spire of English football. Holloway, a Rovers legend as a player, had recently called time on his playing days, and, in his fourth season in charge, was putting the finishing touches to what was widely expected to become a charge towards promotion.

The Pirates were marooned in what was then known as the Football League Second Division (now League One) but were desperate to get back to the second tier after a six-year absence. As a Rovers supporter, you quickly became accustomed to the harsh financial realities of the time. Season after season, Rovers were grappling to stay afloat and usually did so only by selling off what was usually their solitary star player. In the 90’s, this meant the likes of Marcus Stewart, Gareth Taylor, and, at the end of the decade, Barry Hayles all departed the Memorial Ground for fees running into the millions. Despite this, Rovers fans remained an ambitious bunch. They had their eyes set on promotion every time August rolled back around. And as for Holloway; he spoke only about promotion all the way to the Premier League.

In 1999, Rovers were still recovering from the loss of Hayles. Signed from Stevenage for £250K at the beginning of the 1997/1998 season, Hayles was to spend barely eighteen months at the Memorial Ground before being whisked away by a Kevin Keegan-led Fulham for £2 million. Hayles, with 32 goals in 62 games, was a huge loss, and Rovers fell from playoff hopefuls in 1997/1998, to a mid-table side the following year. However, despite the continued loss of his best players, Holloway maintained a remarkable knack for finding yet more rough diamonds to hop onboard the Rover's production line.

After Hayles’ departure, Holloway had gambled £250k, a not inconsiderate sum for the club, on a replacement in the shape of a young Jason Roberts. As the nephew of Cyrille Regis, and having needed convincing to drop down a division from Wolverhampton Wanderers, much was expected of Roberts. First impressions of the youngster were underwhelming. Roberts, physically imposing and pacey, had potential but was raw. Rovers supporters had been spoilt with a recent golden era of striking talent and the £250k figure began to weigh heavily around his neck. Another new signing, Guy Ipoua, a Cameroonian striker signed on a free transfer, managed to dislodge him from the side. Ipoua was willing but limited. Goalscoring was not something that appeared to come easily for him.

Fortunately, the club’s other striker, Jamie Cureton, did not have such problems and, as he would throughout his career, Cureton would continue to find the net on a regular basis. Cureton had been at the club since 1996 but was forced to play out of position on the wing to accommodate Hayles and, another striking gem, Peter Beadle. With Hayles and Beadle now departed, Cureton was finally given the opportunity to lead the Rovers attack and he responded with goals. Lots of them.

There was a sense of anticipation by the eve of the 1999/2000 season. Much of it was built on the back of the previous year. Though Rovers had an inconsistent season and spent most it floating around in mid-table purgatory, but they could really purr on their day. With Roberts having finally settled in and found his shooting boots, and Cureton leading the division’s goalscoring chart, they had the ability to blow any team in the division away when on form. One such example was to be found at the Madejski Stadium where the two strikers ran riot in a 6-0 rout over a fancied Reading team. Rovers were capable of performances like this, but just not consistent enough to put a run together that could take them to the playoffs.

Perhaps it was their style. Since the Holloway era began, Rovers were a strict passing team, with an emphasis on keeping it on the deck at all costs. In a division of bruisers, Rovers were a fish out of water, trying to play their way out of danger. But sometimes it didn't work. As pleasing as they were on the eye, they were equally vulnerable. In the Hayles team, Holloway had a 4-4-2 system with himself, and Gary Penrice (his assistant manager) as the midfield two. Holloway was a lovely player on the ball and spent years in the Premier League starring for QPR. His touch and vision was a class above most opponents he faced in the third tier. Penrice, likewise, had an obvious touch and passing range that was a notch above. He was a converted centre-forward who had played in the top flight too, with Aston Villa and QPR amongst his previous clubs. But Holloway and Penrice were close to the end of their careers and, while they had the desire, the legs weren't there any longer. The centre backs, Andy Tillson and Steve Foster, were often left exposed on the counter-attack and, unless Hayles and co could outscore the opposition, Rovers were often punished.

Holloway appeared to have recognised this, for Rovers changed personnel and brought in a new system. Out went 4-4-2 and in came a 3-5-2 system that suited their personnel to a tee. As philosophies go, this was less Antonio Conte’s Chelsea, and more Roy Evans mid-nineties Liverpool. The flair remained, but the midfield was stiffened considerably. Out went Holloway and Penrice, both retiring to the bench, and in came David Pritchard, Rovers’ right-back by trade, but now transformed into a holding midfielder to great effect. Ronnie Mauge, a tough tackling box-to-box midfielder, came in from Plymouth to add energy and bite and finally David Hillier of Arsenal title-winning fame, joined on a free transfer back in February of 1998 to add the passing vision that had been missing since Holloway's transition back into the dug-out.

The defence had been Rovers’ Achilles heel in the recent past but looked more at home with three solid centre backs. The dependable Steve Foster and the forward-roaming Andy Thomson flanked their captain, the no-nonsense captain Andy Tillson. Behind them, Lee Jones kept watch – a steady if unspectacular goalkeeper.

If Rovers had a weakness it was found in the wing-back positions. Holloway employed either full-backs who didn’t offer enough going forward or tricky wingers who couldn’t handle the defensive aspects of the job. Robbie Pethick who, along with Thomson and Hillier, formed a trio of free transfer signings directly from Portsmouth, usually had the nod on the right side, but it would be a little while until the left wing-back occupant was nailed down.

A new season got underway, but Rovers got off to a slow start, grinding out wins by the odd goal. However, they slowly clicked into gear and by the time the clocks went back in the autumn, they were flying. The muscle memory of the previous season’s successes came back to Holloway’s side and suddenly the goals began to flow. It was an exciting time to follow the club. Rovers at their best were a mesmerising flash of blue and white quartered shirts attacking their opponents from all angles. They appeared to have the perfect blend of solidity in defence, balance in midfield and they might have had the best two players in the division in their attack. Roberts and Cureton patrolled opposition penalty areas like sharks, waiting on the shoulder to run onto a through ball or to pounce upon a mistake. If no mistakes were forthcoming then they both had the ability to produce a goal out of nothing. Roberts could bulldoze his way through defences and finish with aplomb, while the smaller Cureton relied upon outstanding movement and his ability to produce an unerring finish.

By October, with their strikers running amok against Second Division defences, Rovers were top of the league. The following month Holloway pulled off a masterstroke by bringing in the ex-Liverpool and England winger, Mark Walters on a free transfer. Walters was 35-years-old and had been let go by Swindon Town. It looked a curious decision. After all, where was a veteran winger going to be employed in Rovers system? Holloway surprised everybody by lining up Walters as the left wing-back in his fluid 3-5-2. Any concerns about the former Glasgow Rangers man were soon laid to rest by his early appearances. Walters may have lost a lot of his pace, but retained an outstanding technique and vision that was a cut above the rest of the league. By the end of the season, a rejuvenated Walters was to finish the campaign with nine goals from thirty appearances, and these included long-range screamers, delicate free-kicks, and derby winners.

Rovers went into their final game of the millennium having won six consecutive games and on-course to finish in the automatic promotion places. By March they were looking down on their rivals from the summit of the division with the finish line on the horizon. And the goals kept on coming. Twice in a week, they scored four times away from home, shredding their victims, Luton and Oldham, with ruthless displays. By that time, Roberts and Cureton were gaining wider notoriety for their goalscoring exploits, featuring on BBC’s Football Focus to talk about Bristol Rovers and their own rise. And make no mistake, it was certainly justified. This was a team that had a perfect cocktail of a reliable defence and a devastating attack. With ten games to go, Rovers had racked up sixty goals and kept seventeen clean sheets. They were four points clear at the top of the league.

In their next game, Rovers fell to a 2-0 defeat at Reading. Reading were a decent side that season, and despite Rovers appearing uncharacteristically below-par that day, few suspected that it was anything more than a bad day at the office. Instead, it proved to be the beginning of the end for Rovers’ title, and promotion hopes. Their form was to nosedive, winning just one of their final ten games, losing six of them, as they tumbled down the league table. Roberts and Cureton’s goals dried up, and their rock-solid defence began to crumble. On the last day of the season, they needed a win at local rivals Cardiff who, bear in mind, had already been relegated, to finish in the final play-off position. Instead, they lost 1-0 in a pathetic display. Rovers had achieved the unthinkable; from top of the league and entering the home straight, to finishing outside of the playoff positions. This despite accumulating a more than respectable eighty points.

Holloway and the supporters were aghast. They had blown their best chance of promotion in years. It was hard for a supporter to make sense of the collapse. How had a team that was conquering all and sundry, just stopped playing with the finish line in sight? In his autobiography, Ollie, Holloway placed the blame for Rovers’ collapse on three things; injuries, his own inexperience as a manager, and a loss of focus from his key men. But still, there was a sense of bewilderment in his words: “Why had we fallen away so badly? I’m not entirely sure, to be honest, but injuries to key players in key games cost us dearly, but I got blamed for the poor run and, as a manager, you put yourself up there to be shot at and my ass had been peppered with buckshot.”

It was true that Rovers suffered some bad misfortune with injuries. David Pritchard, their midfield anchor, went down in January with an injury that was eventually to bring his career into early retirement. Mauge, their other midfield enforcer, was absent, too, with injuries and international call-ups with Trinidad and Tobago. Holloway was forced to bring wingers out of position to cover their absence, and Rovers were suddenly a much more vulnerable team without their midfield shield.

Rovers cause wasn’t helped by Cureton and Roberts' form trailing off quite noticeably during the run-in. Holloway believes that they both may have had heads turned by constant press speculation concerning transfers to bigger and better clubs. In Ollie, Holloway shares: “There was a lot of political stuff surrounding Jason (Roberts) as we entered the final straight of the campaign. I think his family wanted him to move on because he was scoring goals and he and Cureton were constantly being talked about and linked with moves away.”

It’s interesting to read Holloway describing an incident in which a former player of the club, Peter Beadle, now representing Bristol City, came to their training ground one day in the spring, and was found by Holloway in the kit room deep in discussion with both Cureton and Roberts. Beadle was talking about his new contract at City. He was earning good money at Rovers’ rivals, much more than what Rovers were paying their own two strikers. Holloway lost his temper, promptly kicking Beadle out of the training ground. Holloway reflected: “From that day on, I think I lost a piece of both players and something changed. It was hard for them when they were playing at the top of their game and were being paid what they were. Then, when somebody who isn’t playing that well signs for your neighbours, and gets three times as much, you’re not going to put up with that for long are you?”

Another decision that Holloway blamed on his inexperience as a manager, was the decision to immediately restore Roberts to the starting line-up upon his return from international duty with Grenada back in late January. In the striker's absence his young deputy, Nathan Ellington, had produced a flawless performance and scored two goals in a 5-0 rout away at Oxford United. But Holloway felt that he couldn't keep his star striker on the bench upon his return, particularly with the rumours beginning to swirl that he was already unhappy at the club. Roberts was restored and resumed scoring duties but it was a decision that Holloway later reflected alienated the dressing room to a degree. The players, already tired of hearing that they were a two-man team, wanted to see the manager make a stand against their teammate.

Whatever the reasons behind Rovers’ devastating collapse that season, it was to be the last opportunity Rovers would have for quite some time. For Holloway, the rot had set in. Cureton and Roberts left that summer having both handed in transfer requests shortly after the final game of the season. The following year, short of their goals and with Holloway’s magic touch in the transfer market having deserted him, the team started to slide down the table. Injuries and Father Time decimated the remainder of the previous season’s side and by February 2001 Holloway was gone.

His replacement, Gary Thompson, couldn’t arrest the slump and, quite unbelievingly, Rovers found themselves relegated to the fourth tier of English football for the first time in their history. Eighteen years on from the 1999/2000 season, they have yet to hit the same heights that the Holloway team achieved, though their current manager, Darrell Clarke, has performed admirably with the current squad, achieving back-to-back promotions from the Conference, through to League One again.

The team that Holloway coined, “Total Football Rovers-style” is still remembered fondly by many supporters. But there’s a regret of ‘what might have been’ that hasn’t yet gone away. It’s worth noting that there were seven teams in their division that year that later went on to reach the Premier League promised land; Stoke, Burnley, Wigan, Reading, Cardiff, Bournemouth and Blackpool. The Bristol Rovers team of 2017 is quite different to Holloway’s charges. There’s not a Cureton or a Roberts. The team is more than the sum of their parts. They’re hanging onto the coattails of the play-off positions, just about. But until they, or a future group, can escape the division, the ghost of the 1999/2000 season is still one that has to be laid to rest.

By David Tully