In 1967/8, you’d forgive City’s players and supporters if they said they’d had their fill of Middlesbrough. Already in the same division, the two were then paired in the FA Cup third round draw and took an age to find a winner between them. And ultimately, they would play five times through the season without City succeeding once.
Hopes remained high for City as the late 60s appeared. The legendary promotion from the Third Division in 1966 had been followed by a storming start to Second Division life before the 1966/7 campaign tailed off. Again, there was belief that the iconic five-strong strikeforce would be good enough to score the goals to challenge for a first-ever top flight place when 1967/8 began, even though louder doubts were now being expressed about the lack of strength, depth and out-and-out talent at the back.
By January 1968, City were showing some capability of transition. Andy Davidson had, after 520 games, suffered his career-ending injury just two months before and the sprightly Frank Banks was proving a worthy replacement. A mild concession had been made to the ‘all for one, one for all’ policy via the deployment in midfield of Billy Wilkinson as an extra stopping presence, with ageing winger Ray Henderson finding himself on the bench a lot as a result.
Boro had been relegated the year before but under the youthful Stan Anderson, had bounced straight back up. They were more serious contenders for promotion than City by the time FA Cup draw was made, and home advantage further strengthened their position as pre-match favourites.
The first chance of the match fell to striker John O’Rourke, who was released by winger Mike Kear in the opening second and keeper Ian McKechnie, showered with oranges as ever by the travelling City fans during the kick-in, made a very smart stop at his near post.
Ian Butler then headed a Ken Houghton corner just wide from City’s first go at goal, then Wilkinson had a shot blocked from a tidy Ken Wagstaff knock-down.
Bill Gates then headed a Chris Simpkin centre over his own bar under pressure from Chris Chilton, as City began to pile it on. An obstruction in the box on Wilkinson led to an indirect free kick, the build up to which was described in the Sports Mail match report as “something of a pantomime” before, eventually, Houghton slammed a shot into the wall.
Chilton then volleyed a Banks cross over the bar, then helped himself to the opening goal on 37 minutes when a cleared Boro corner allowed Simpkin to deliver a 50 yard pass for the big forward to chase. He brushed away the challenge of Gates before sliding a confident shot past Willie Whigham in the Boro goal.
Three unmarked Boro forwards raged at Kear shortly afterwards when he allowed Banks to tackle him as they awaited a cross. At the break, City were a goal up and looking considerably the more accomplished side.
O’Rourke was subbed at half time, to be replaced by Arthur Horsfield. The injury he suffered ended his season and he never played for Boro again. Horsfield made an instant impact with a ball for John Hickton to chase and he and McKechnie clattered into one another so vehemently that the City keeper ended up head first in the terraces behind his goal.
Houghton miskicked a good chance from the edge of the box and City were made to pay when, after just five minutes of the second half, the home side levelled up. Tom Wilson’s weak back pass was intercepted by Hickton whose collision with McKechnie took the City keeper out of the picture. Inside forward Johnny Crossan followed up to bury the ball into the empty net, though Paddy Greenwood, like Banks playing his first ever FA Cup tie, very nearly kept it out on the line.
Ian Butler headed a Simpkin free kick just wide shortly afterwards but then Boro were given a great opportunity to take the lead when a foul by Greenwood on Hickton resulted in the award of a penalty. Hickton took it himself but McKechnie’s agility won the day, diving full length to his right to parry the ball and then land on it at the second attempt as a despairing Hickton, who’d never missed a spot kick before, came in for the rebound.
Ian Butler then headed another chance at goal, this time from a Banks run and cross, and Whigham saved it well. McKechnie at the other end then plucked a Dave Smith cross out of the sky as Horsfield closed in.
City could have won it with two chances from the oddly out-of-sorts Houghton going begging. He dillied and dallied on the ball from a Banks cross and allowed Frank Spraggon to relieve him of the ball, then late on Wagstaff sent him clear with just the keeper to beat and a meagre four minutes left to play, but he aimed his shot wide.
Whigham saved from a Gates miskick in injury time as City tried to grab a dramatic winner, but in the end a 1-1 draw was deemed fair in a bruising encounter.
Six players were carrying injuries but the medical team worked overtime on getting them fit for the replay four days later. Wagstaff put City 2-0 with a brace in the opening 26 minutes but Horsfield, starting the game as Anderson made three changes, scored two of his own to force a second replay on neutral territory. This was initially earmarked for Hillsborough, but a cut-up pitch and heavy South Yorkshire snow forced a late change to York’s Bootham Crescent for the game, just 24 hours before it was due, and Boro won it with a single goal from Derrick Downing. It was the only time they had been ahead in the tie.
City’s team was very familiar, with Ian Butler, Chilton, Wagstaff and Houghton still at the peak of their powers. Wilkinson, who was from Middlesbrough, was a newer kid on the block though had been at the club six years by the time he began to hold down a more regular place in the side. Banks and Greenwood were good signs of things to come; Dennis Butler a sturdy long-term presence in defence; Simpkin similarly approaching stalwart status in the middle of the pitch and McKechnie the popular, erratic, talented scurvy-dodger behind them all. The team didn’t change for the three FA Cup clashes, with Henderson getting on for the injured Wilkinson in the third game. The only non-regular in the side was new signing Wilson, a gruff Scottish defender who’d come in from Millwall. He didn’t miss a game for the rest of the season after his debut in November 1967 but was in and out for the subsequent two campaigns before dropping into the non-league game. His association with City as coach, caretaker manager and secretary would become the stuff of legend to the generation of supporters that followed.
In the midst of this marathon was a league game to muddy the waters too (“the Second Division filling in the FA Cup sandwich”, as the Hull Daily Mail had it), which took place between the first and second replays. City lost it 2-1 at Ayresome Park, having made a number of changes to protect players for the FA Cup game (a mirror opposite of what would happen today). Ron Young, one of the beneficiaries of Cliff Britton’s rare use of squad rotation, got the Tigers’ goal, while young striker from the ranks Ian Davidson was given his first start for the club.
Boro had also won at Boothferry Park in the September, giving them unquestionable bogey status over the Tigers that year. They finished sixth in Division Two, City ended up 17th. Boro went on to lose to Bristol City after a replay in the next round of the FA Cup; their exit in the last 32 came despite playing the quantity of FA Cup football that would normally result in an appearance in the final.
The two sides had previously played twice in the FA Cup, and each prevailed once. City battered Boro 5-0 in the third round of 1921/2, while Boro came through a tougher encounter in 1947/8 at the same stage, eventually winning 3-1. There was also a more recent bout in the competition between the two, when a late Nicky Forster goal gave City, at the time struggling in the Championship, a 1-1 draw in the third round at the KC, with the then Premier League side triumphing 4-3 in a replay at the Riverside memorable for Andy Dawson’s only brace of goals (containing within it his only headed goal) for City and the Tiger Nation extracting the hug and kiss out of Boro’s over-exuberant music-after-goals usage.
Four league games – one in the Premier League, three in the second tier – have followed between the two at the Riverside and the upshot is that City have still never won there. It’ll be a rare, if not unique event this weekend for City to go to Middlesbrough as favourites for the first time since Boro quit Ayresome Park, though as it’s City in the FA Cup, nothing is ever certain.