The football ground has hosted many matches where silverware has been at stake. These include the Boston Hospital Cup - most notably a 4-3 win against Aston Villa in May 1946 and a loss against Ipswich Town a year later; the Mather Cup - including wins against Sheffield United, Leeds United, Southampton and Derby County; the Northern Premier League Challenge Shield - an early season match between the previous season's League Champions and League Cup winners which Boston won at York Street in 1974 beating Wigan Athletic 2-1 and again in 1977 against Scarborough. However, the trophy that Boston United have won more times than any other at Shodfriars Lane / York Street is the Lincs Senior Cup. United have won this cup seventeen times and thirteen of those wins were from cup finals at their own ground.
The first win came against Grantham in 1935. That season in games at Shodfriars Lane Grantham had already gone down 4-3 in the Midland League and had been knocked out the FA Cup 3-1 so it was no surprise when Boston also came out on top in the Lincs County Senior Cup final 3-0 in front of an impressive crowd of 5,500. The Boston goals were scored by Eddie Earle, Frank Bungay and Billy Marshall. A year later Grantham were again their opponents in the final and this time Boston won 4-1. In 1938 Gainsborough Trinity were beaten 2-0 in the final for Boston's third County Cup title.
Immediately after the Second World War watching football was extremely popular. When Boston United reached the final of the Lincolnshire Senior Cup against Grantham in 1946 they attracted a record crowd of over 8,500, and this didn't include spectators watching the game from nearby trees and roofs! Boston opened strongly but against the run of play Grantham took the lead when a shot by Bradley gave Hammond no chance. Grantham then came close to doubling their score when a shot from Macartney grazed the crossbar. End to end play followed with good chances for both sides. Boston scored next just before half-time. Tommy Mitcham broke down the wing, crossed to Harry Sharp who flashed the ball into the net. Four minutes into the second half Boston went in front. With the Grantham defenders concentrating on marking Sharp, this left Roy Houghton free to bang in an unstoppable shot. A few minutes later Boston went further ahead with a glorious goal. Tommy Mitcham weaved his way through the entire Grantham defence before finishing with a powerful drive. This was the last goal of the match although Boston came close to scoring when a shot from Bill Pate hit the underside of the bar before bouncing out. Boston also had a handball penalty appeal turned down. Boston finished as 3-1 victors.
Another memorable Senior Cup final at York Street was in 1976. The cup was reorganised for the season. The competition was split into two groups, with the county's three League sides in one group and the top three non-league sides in the other. Lincoln City progressed to the final by winning away at Grimsby and Scunthorpe. Boston beat Grantham away and Gainsborough at home.
The final at York Street gave the Pilgrims a chance to gain revenge for a narrow 1-0 defeat to the Imps in the previous season's FA Cup. The Lincoln team contained only two changes from that which had won the FA Cup game. The Boston side had six new faces. In defence Dave Poplar and Peter Johnson had replaced Dave Coxon and Colin Symm. The midfield now had two outstanding youngsters in Lawrie Madden and Steve Thompson, both of whom would later play at a much higher level. Up front, Gordon Bolland and Andy Gilliver had made way for Peter Wilkey and Bobby Brown.
|Boston were a goal down after just six minutes when Boston keeper Gerry Stewart dropped a half-hit shot from Dave Smith and John Ward pounced to slot home. Three minutes later Peter Wilkey equalised for Boston with a stunning 18-yard shot through a crowded defence. On twenty minutes Boston took the lead when Jim Kabia dispossessed former Charlton midfielder Dennis Booth and took the ball forward before planting a low shot between the keeper and the post. On sixty minutes Boston made sure of the result when Steve Thompson took a long throw in from the left, which was headed across the face of the goal by Dave Poplar allowing Bobby Brown to nod home. Both managers - Howard Wilkinson and Graham Taylor - would go on to manage the England team later in their careers.||
With the 2019/20 final between Boston and Cleethorpes Town being played at Sincil Bank that makes United's 2-1 win over Scunthorpe United in 2006 as their last ever Lincs Senior Cup final win at York Street. Peter Till and Danny Thomas got the Boston goals.
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