How Middlesbrough Inspired Chelsea's Legacy of Trophy Success

As Chelsea begin to hint at being a club on their way to restoration with Antonio Conte at the helm, it's apt they come to blows with Middlesbrough this weekend. After all, when we think of the Blues' trophy success in the past 20 years, Middlesbrough is where it all began.

Before Roman Abramovich arrived, Chelsea were winning things, and Boro were helping them do it.

The parallels between Chelsea then and now are striking. In 1996/97 an Italian core had put Chelsea back on the map. With Roberto Di Matteo, Gianfranco Zola and Gianluca Vialli in their ranks, the Blues were reborn as a force in the English game.

Now it's their compatriot Conte who is breathing life into a team that this time last year seemed well beyond its sell-by date. Yes, Chelsea were reigning Premier League champions, but their sudden and immediate downfall confirmed the long-held concerns about an imbalance within the squad and a lack of direction.

Even with Messiah Mourinho at the helm, things were not quite right. Losing Jose in the manner they did was painful; fans didn't want the love affair to end, but the sad truth is that it had to. It had been soured beyond saving, and now Conte has been given licence to resurrect the club.

Twenty years ago, the pain Chelsea had endured lasted much longer than 12 months. It had been a lot more than 12 seasons, in fact. Not since the 1970s could we take seriously the club's silverware ambitions. There had been the odd flirtation with success—like in 1985/86, when Chelsea finished sixth in Division One but as late into the season as March had been among the title contenders—yet it was never sustained.

Within two years, Chelsea would be relegated to Division Two, demonstrating how the club lived a feast-and-famine existence. Even promotion back to the top flight in 1989 didn't spell the end of Chelsea's flirtation with success and failure. Relegation remained a threat, and despite reaching the 1994 FA Cup final, the Blues had been looking dangerously over their shoulder at a potential scrap at the bottom of the Premier League.

It would be three years later that it would all change. Di Matteo scored on his home debut for the Blues against Middlesbrough and the mood suddenly flipped. The revolution that had been hinted at ever since Glenn Hoddle was appointed boss in 1993 had arrived. The Blues had a different swagger about them, especially with Ruud Gullit now in the dugout as Hoddle left for England.

He may have been Dutch, yet Gullit's best years as a player were spent in Italy with AC Milan and Sampdoria. The culture of Serie A had made a lasting impression on him, and Gullit embraced it; he signed Italians to energise his team.

Di Matteo's goal in a 1-0 victory represented just three points on the board that August night. That's the only view to take in a tangible sense; symbolically, however, it represented so much more.

Beating Middlesbrough at Stamford Bridge was about breathing confidence into what Gullit was attempting to achieve. He was a new manager, still playing a bit-part role as a player for Chelsea. Appointing him had been a risk.

When Gullit was signing players from overseas en masse—Frenchman Frank Leboeuf also joined the club in the summer of 1996—eyebrows were raised. Foreign names were creeping into the English game, but the way Chelsea were operating, it felt like an invasion.

Gullit needed his regime to pick up pace. Quickly. When Di Matteo rocketed his effort into the back of the net in front of a building site where the old Shed End had once stood, it was the sort of positive twist every new manager craves. Four minutes later, the game would have been over. The mood would have been different. Chelsea had drawn their opening league game with Southampton; they needed to win their first Gullit match at home.

Indeed, mention of the Shed End's redevelopment is interesting. Di Matteo's goal was about progress on the pitch, and the cranes that now stood in place of the terraces were about everything that was going on off it. This was a new Chelsea, even if the advertising boards behind the goal were decorated in a red-and-blue striped tint that resembled the colours of south London rivals Crystal Palace.

As much as the Shed was a staple of what made Chelsea Chelsea, it was still a relic. The old terrace was from a bygone age, and as a club, the Blues were too in some regards. They hadn't won a major trophy since 1971, meaning a couple of generations of supporters had been raised on past glories. The stories being passed down were feeding any passion for glory.

So Di Matteo's goal against Boro was about plenty more than the three points he won. It was the moment that built Chelsea's entire campaign. The foreigners meant business.

By May, we saw the result of that. Middlesbrough were the opponents again, and this time, the stage was far more significant: It was the 1997 FA Cup final. Di Matteo couldn't wait 86 minutes to deliver glory this time; he didn't even wait one. Within 41 seconds, he had rocketed a pile-driver beyond goalkeeper Ben Roberts to put Chelsea in front at Wembley.

Bryan Robson's side had provided the platform to start the season, and now they were the foundation for a legacy. Chelsea would win 2-0, Eddie Newton bundling home to double his team's lead after an assist from another of the Blues' Italians, Zola.

In more recent times, Mourinho has spoken about the importance of winning that first trophy for any group of players. His philosophy has been about creating a collective feeling of success. Every team will have its stars and those who are most vital, but every player has to feel like a champion.

When Chelsea won the 2005 Carling Cup, Mourinho had chased the glory for those reasons. He wanted that trophy to be his first in English football simply because it was the first he could win. The Premier League would then come.

For a club that hadn't been used to winning things, defeating Boro in May 1997 came indoctrinated in those same principles. It would be seven years before Chelsea fans would see Mourinho at the club, but without Middlesbrough, there's every chance they wouldn't have done.

No FA Cup success in 1997 would have potentially meant no Coca-Cola Cup and Cup Winners' Cup success in 1998. The domino effect of that suggests no Champions League in 1999/00 and also no Jesper Gronkjaer to score his goal against Liverpool on the final day of 2002/03. That bit of history led to Abramovich's arrival, which has ultimately put Chelsea where they are now.

Middlesbrough was where the journey started. Even less than a year later, that 1998 League Cup victory was also at Boro's expense, Chelsea again winning 2-0 when they faced Robson's men beneath Wembley Stadium's old twin towers.

And now, here they are. Boro are back in the Premier League and face a Chelsea side attempting to restore the foundations that were shaken so violently last season.

Will we witness another moment of significance in Chelsea's history at the Riverside on Sunday?

Garry Hayes is Bleacher Report's lead Chelsea correspondent. Follow him on Twitter @garryhayes