In May 1988 Mauricio Pochettino was a 16-year-old youth-team player at Newell’s Old Boys in Argentina and Michael Carrick, although still only six, had been kicking footballs at Wallsend Boys Club for two years. Fast forward and the pair are preparing for technical-area tactical combat at Stamford Bridge, where Pochettino’s Chelsea will kick off Tuesday’s Carabao Cup semi-final second leg trailing Carrick’s Middlesbrough 1-0. Much may hinge on whether the visiting right-winger Isaiah Jones passes a late test on a strained hamstring and is able to attempt to reprise his man-of-the-match performance at the Riverside two weeks ago. Although the Championship side remain underdogs, Boro fans of a certain age remember the last time they visited Chelsea for a pivotal second-leg fixture with the home side cast as firm favourites. Thirty-six years ago the then recently introduced playoffs involved the side that finished fourth bottom of the old First Division competing against the third-, fourth- and fifth-placed teams in the second tier. With Middlesbrough, third in the old Second Division, having beaten Bradford in the semi-final, and top-flight Chelsea ending Blackburn’s challenge, the first leg of the final at Ayresome Park ended with Bruce Rioch’s Boro 2-0 up against Bobby Campbell’s team. Given that Chelsea possessed the attacking talent of Pat Nevin, Kerry Dixon and Gordon Durie and a Boro team largely comprising young homegrown Teessiders had emerged from the third tier – not to mention a liquidation scare – only a year earlier, Stamford Bridge regulars retained considerable confidence. Yet despite a stellar performance on Nevin’s part and a goal from Durie, a Boro team including Gary Pallister, Tony Mowbray, Colin Cooper, Bernie Slaven and Stuart Ripley clung on to secure a 2-1 aggregate victory. Chelsea’s relegation did not go down remotely well in the Shed End and, at the final whistle, hundreds of home fans invaded the pitch in an often violent incursion which prompted Rioch’s players to sprint towards the sanctuary of the tunnel. “I’d never run so fast in my life,” said Slaven after 40 minutes of mayhem, eventually involving the deployment of mounted police. There were 102 arrests and 45 notable injuries, including 25 sustained by police officers. Boro’s staff and players spent an hour locked in the away dressing room before being advised it was safe to finally celebrate on the pitch. Chelsea were fined for inadequate stewarding and Stamford Bridge’s terraces were closed for the first six games of the following season. Meanwhile the Football Association quietly scrapped plans to lobby Uefa for a lifting of the ban on English clubs participating in European competitions imposed in the wake of the Heysel disaster and Nevin joined Everton. At the time Bryan Lonsbrough, the then mayor of Middlesbrough, told Teesside’s Evening Gazette: “I now know how the Christians felt in the arenas of ancient Rome up against the Lions.” The late former Middlesbrough MP Stuart Bell described the pitch invasion as “like the hordes of Genghis Khan”, and the Gazette’s then chief football writer, Eric Paylor, spoke of “a deep sense of hatred” underpinning what he would subsequently describe as “the ugliest atmosphere I can remember at a game”. Well over three decades later, hooliganism, at least inside English stadiums, is mercifully a thing of the past but Chelsea supporters appear optimistic that their expensively assembled team can overturn a lead established by Hayden Hackney’s first-leg winner on a night when Pochettino’s £200m-plus midfield was frequently outmanoeuvred by Hackney, Dan Barlaser, Jones and company. While Pochettino is desperate to camouflage a difficult first season in charge of Chelsea with a trophy, playoff-chasing Boro dream of reprising their 2004 League Cup final triumph against Bolton. “The boys are hugely looking forward to the game,” says Carrick, whose side are 11th in the Championship but only three points adrift of the top six. “It’s a great challenge for us to embrace.” As a Manchester United midfielder, Boro’s manager won three League Cups but his team will be weakened significantly by a series of largely injury-induced absences. That casualty list has left Carrick low on counterattacking pace, a problem that will be exacerbated should Jones fail his fitness test. “It won’t be a copy-and-paste performance from two weeks ago,” Carrick says. “There’s going to be different challenges. We expect the best version of Chelsea. We know what we’re getting into; we’re going to face individual quality and collective strength. “Getting the right balance between protecting our lead and attacking is tough but we want to win again on the night. It’s going to be about managing the game and its momentum. It about how we can be the best version of ourselves.” Like Carrick, Rioch, himself once a fine midfielder, created an attractively sweet-passing Boro team. Although they survived only one season in the top tier, his achievement in winning the so-called “Battle of Stamford Bridge” propelled him into the managerial limelight, arguably helping secure, albeit briefly, the Arsenal job in 1995. Carrick knows that reaching a Wembley final possesses similar potential to sprinkle stardust on an already promising coaching reputation. “I’m not getting carried away, we’ve got an awful lot of work to do,” he says. “But winning at Chelsea would mean an awful lot.”