The Pilgrims had won 2-0 away to fourth division Southport while the Minstermen, also of Division Four, required a replay to get past Tamworth.
The game, played at York Street in front of 6,218, saw United go ahead through Brian Bates on the quarter hour- a lead while lasted until the final 10 minutes.
Ian Davidson bundled home the rebound after John Lakin had cleared off the line from a free-kick, then with four minutes left City had a penalty.
Billy Howells, a Boston man since 1966 (he would become the club’s record appearance holder with 572 - a record surpassed by Paul Bastock in 2002), objected to a challenge in the area by Brian Swallow on goalkeeper Malcolm White, and kicked the forward.
He was sent off, and John Mackin scored the spot kick.
Howells said after the game: "It was the most stupid thing I have done in my life!”
Manager Jim Smith exclaimed: "It was thrown away, one goal from a footballing error, the other from a human error.
"It was diabolical… I feel very sorry for the supporters, they were let down.”
The sides then waited 32 years before facing off in a first league meeting between the two.
United’s promotion to Division Three saw them face York during their season as York City Soccer Club (2002-03).
Both clubs won at home, a 2-0 scoreline thanks to Peter Duffield and Lee Nogan at York on August Bank Holiday Monday was avenged by a Stuart Douglas brace and Richard Logan’s goal in a 3-0 Boxing Day win for Boston.
The following year City were relegated, taking a point at home to Boston (John Parkin and Simon Weatherstone cancelling each other our) in a game which Adebayo Akinfenwa featured for the visitors, before a 2-0 defeat at York Street.
Duffield, a goalscorer in red the season prior, netted for Boston, alongside Graeme Jones.
A snowy afternoon in December 2010 brought the next competitive clash between Boston and York, an FA Trophy tie won by Spencer Weir-Daley’s 15th minute goal for Northern Premier League United at Bootham Crescent.
The 164 visiting fans watched what would be the Pilgrims’ only game of December.
City’s relegation to Non-League’s second tier in 2017 signalled a return to league contests between the sides, the first proving to be Craig Elliott’s first win in the Boston dugout.
His side overturned an Adriano Moke goal with second half strikes from Jordan Keane and Ashley Hemmings.
The reverse fixture, another wintery scene at Bootham Crescent saw Ferguson win City the points as Simon Heslop (York, but later Boston), Andi Thanoj and Ben Middleton (both Boston) all saw red late on.
United again won their home game with York in 2018-19, Nicky Walker and Gavin Allott netting a dozen minutes apart in Decmeber, while the reverse fixture saw 260 Boston fans witness all four goals at their end - Shaun Newton and Macauley Langstaff earning a first half lead for the hosts before Jay Rollins and Max Wright rescued a point.
The Covid-curtailed 2019-20 season lasted long enough for eventual second and third placed City and United to exchange home wins.
A Tuesday night in October saw Alex Kempster and Jordan Burrow render Rollins’ effort mere consolation, while the last York Street meeting between the sides saw Kurt Willoughby’s seventh minute goal countered by Frank Mulhern’s bizarre scoop in the first half, then Brad Abbott and Andi Thanoj eased United to victory.
The sides did not meet behind closed doors, York missing out on hosting Boston in the play-off final as both sides ultimately lost to Altrincham in the play-offs of July/August 2020, then United completed a first league double over the Minstermen this season.
Penalties from Danny Elliott and Shane Byrne sealed the points in front of 2018 at Pilgrim Way, Michael Woods having levelled for the visiting City, before Elliott curled in the game’s only goal at the York Community Stadium in March - almost 3,000 in attendance.
Boston’s early history had seen them face York City Reserves in 12 Midland League seasons - the second City side never able to win away from home.
United picked up 13 wins to City’s seven, with four draws exchanged, as the sides scored a remarkable number of goals across the 24 matches – Boston 71 and York 48.
Scorelines included 7-2, 6-2, 6-4 and 6-0 wins for United, a 4-4 and two 3-3 draws, and a 6-0 York win.
The 6-0 Boston win, in November 1950, saw Jack Stone net five times (one of just five occasions a Pilgrim has managed this).