Back in 2008, an awful quarter-final loss for Boro - then in the Premier League - to Championship side Cardiff prevented them from reaching Wembley in a season when the big guns all tumbled out of the FA Cup early and Portsmouth went onto lift the trophy.
In 2020, a similarly wretched league defeat to Swansea proved the managerial death knell for Jonathan Woodgate, sacked in its aftermath with Neil Warnock brought in to save the ailing Teessiders from a highly probable relegation to the third tier for the first time since 1986.
Ahead of this particular occasion against opponents from the Principality, Chris Wilder spoke of it being a ‘season-defining game’ for Boro if they were to maintain their hopes of breaking into the top six in the nick of time.
It was not a night without its imperfections in a game when Boro’s strikers again failed to find the net. Crucially, two midfielders in Marcus Tavernier and Riley McGree, who scored his second goal in successive games and first at the Riverside, did.
Adding to the positivity is that top-scorer Matt Crooks - a goalscoring midfielder with nine goals this term - is back from suspension for the weekend game in Stoke, while key defender Dael Fry should also be available.
In the here and now, Wilder’s side answered his call and kept their season alive to move within two points of his former club Sheffield United, who occupy the final play-off place with two games to go and keep it in the melting pot.
Job done, as Wilder remarked afterwards after his side secured their first win in six matches to move up two places to seventh - and also end a morale-sapping three-match Championship losing sequence on home soil and goal drought in the process.
Wilder spoke about the importance of being good in both boxes and while Boro could have registered more than two goals, two is progress.
In the defensive realm, the likes of Sol Bamba, immaculate against his former side and who nearly scored at the end - and Anfernee Dijksteel, who made a key late block to help secure a clean sheet for the hosts - were strong and put their bodies on the line. Jonny Howson also led by example and had a hand in both goals.
With a win or so much as a goal on home soil since early March, Boro looked in need of inspiration in the first half and the breakthrough fortunately arrived at a timely juncture just before the half-hour when some frustration was in danger of creeping in.
The hosts’ most fluid move of the half ended with the ball in the back of the net as Wilder’s side scored their first goal at the Riverside in all competitions in just over six-and-a-half hours.
It was started by McGree close to the right flank and some neat combination play between Howson and Flo Balogun found Tavernier in space and he unleashed a low 20–yarder which beat the defences of Dillon Phillips.
Wilder clapped his hands in appreciation following a well-crafted goal after Boro afforded themselves a much-needed breakthrough after struggling to pick the lock before that.
Yet in a first-half in which the other substantive chances were carved out by Cardiff, with Boro struggling to get handle Wales international Rubin Colwill, who operated just before the front two of Jordan Hugill and Max Watters, in particular, the emotion at the interval was one of relief for the hosts.
On another day, they could have easily been behind following a decidedly streaky half and with that came the realisation that there was a need to grab a second goal on the restart to provide themselves with a touch of respite.
Refreshingly, it came from Boro and McGree.
In the first half, City had three good chances. The first, before Boro opened their account, came when unmarked defender Oliver Denham planted a downward header straight at Daniels from Tommy Doyle.
Shortly after Tavernier’s strike, Watters tamely shot at Daniels after being picked out by Colwill, who was also the creator moments before the break for former Boro season-ticket holder and loanee Hugill, who fired a crisp shot over when well positioned..
Cardiff had done enough to keep them very much interested. But McGree’s second deflated them.
It came when a loose play by Leeds loanee Cody Drameh was seized upon by Howson who found the onrushing McGree, whose shot took a significant deflection off Curtis Nelson before finding the net.
At the other end, Watters’ rising shot was tipped over by Luke Daniels before the ex-Doncaster Rovers forward’s fluke cross clipped the bar. It was not Cardiff’s night, fortunately and the last half-hour was pretty much a cruise for Boro.
Middlesbrough: Daniels; Dijksteel, Bamba, McNair; Jones, McGree, Howson, Tavernier, Bola, Watmore (Connolly 76), Balogun (Sporar 61), Substitutes unused: Lumley, Hall, Payero, Peltier, Coburn.
Cardiff City: Phillips; Drameh, Nelson, Denham, Ng; Wintle, Vaulks, Doyle; Colwill; Hugill (Collins 80), Watters (Harris 63). Substitutes unused: Luthra, McGuinness, Flint, King, Semenyo.
Referee: M Donohue (Greater Manchester).