Their first game was a 3–1 defeat at home to Grimsby Reserves on 26 August 1933, when a crowd of 1,544 watched Boston's no.7, Blessed, score United's first ever goal.

The club's FA cup run of 1955–56 included a 6–1 victory at Derby County, then playing in Third Division North, with Geoff Hazledine scoring a hat-trick.

In 1985, Boston United went to Wembley for the first and only time in their history for the FA Trophy Final of the 1984–85 season, after Bob Lee scored a winning last minute goal in the 2nd leg of the semi-final against Altrincham at York Street to put the Pilgrims through.

However, in the wake of their promotion, Boston's manager, Steve Evans, and former chairman, Pat Malkinson, were charged with breaking the Football Association's rules over the registration of players.

Evans' return and a substantial investment in the playing squad saw Boston among the promotion favourites for the 2004–05 season, but it in fact resulted in a disappointing 16th place finish.

This would be United's first season under the new ownership of David Newton and Neil Kempster, who took control of the club over from ex-Chairman Jim Rodwell.

A much more favourable campaign the following season saw the Pilgrims finish 3rd in the league where they won the play-offs, beating Bradford Park Avenue in the final thanks to an Anthony Church extra time winner to earn promotion back to the Conference North.

Club chairman David Newton revealed he was beginning legal proceedings against the pair and Grimsby Town for breach of contract.

With only seven Conference North games remaining, the pair guided United to a 3rd-place finish in the league setting up a play-off tie against Guiseley.

Dennis Greene took over soon afterwards, but after a good start could not help the club from finishing higher than a poor 16th place, just 5 points above the relegation zone.

With Boston occupying a relegation spot, Craig Elliott – leaving Shaw Lane to do so – took over and guided the Pilgrims to safety.

A draw at Spotland secured York Street one last big cup tie – the League One side winning 2–1 in a televised replay with over 4,000 in attendance.

The coronavirus pandemic cut short the season and Boston finished third on points per game, winning a behind closed doors semi-final against Gateshead 5–3 to secure a play-off final with Altrincham.

With the new Pilgrim Way stadium delayed due to the pandemic, the 2020–21 season, still behind closed doors, started with United playing home games at Gainsborough's Northolme.

[7] For the beginning of the 2020–21 season, the club were granted permission to use Gainsborough Trinity's Northolme as their home ground temporarily whilst finishing touches were applied to their new stadium.

[8] The club played its first game at the Boston Community Stadium on 5 December 2020, resulting in a 2–0 home defeat to Chorley in the National League North.

I would urge all supporters and anybody interested in the future of the football club, be that investors or potential purchasers, to come forward immediately".

In November 2006, Boston manager Steve Evans and his former chairman Pat Malkinson pleaded guilty to "conspiring to cheat the public revenue between 1997 and 2002".

Chief executive John Moules released this statement: "Because Boston United are in breach of certain rules, it was felt Blue Square North was the best place for them.

On 4 July 2007, Chestnut Homes, a local housing development company, announced that they had acquired Boston United FC.

[12] In a statement at a press conference the new chairman David Newton said: "... we are happy to sit here today and make certain pledges to the loyal supporters of the club.

"[13] During the summer of 2007, Boston lost their entire squad except for Stewart Talbot and Paul Ellender, and new manager Tommy Taylor had to start from scratch.

Nevertheless, at the end of the season it was announced Boston would be expelled from the Conference league structure after the club failed to exit administration by 10 May deadline.

After World War II, Boston United reverted to blue shirts of different shades with either black or white shorts and socks.

[14] Table of kit suppliers and shirt sponsors appear below:[15] Note: Flags indicate national team as defined under FIFA eligibility rules; some limited exceptions apply.