The competition can be traced back to the formation of the Lincolnshire FA at a meeting held at the Queens Hotel in Lincoln on Saturday 17 September 1881[1] and sixteen teams entered the inaugural Lincolnshire Cup competition with Spilsby the first winners in 1881—82.

[3] The elevation of Grimsby Town and Lincoln City to the Football League in 1892 and Gainsborough Trinity in 1896 saw the importance of the competition decline over time and the format has undergone a number of changes over time as has the type of trophies offered by the Lincolnshire FA.

The final was not played in the 1887–88 season after finalists Grimsby Town resigned from the Lincolnshire FA.

The senior non-league sides continued to play for the 'Lincolnshire County Senior Cup' (LCS) and this continued to attract strong interest for these sides with, for comparison, the 1934–35 final replay between Boston United and Grantham attracting an attendance of 5,500.

Scunthorpe United's elevation to the Football League saw them eligible to participate in the competition from 1951 to 1952 onwards.

From season 1949–50 onwards the Lincolnshire County Senior Cup split into two sections 'A' and 'B' and was restricted to clubs nominated to compete.

[21] In 1956 the Lincolnshire Senior Cup competition was expanded to four clubs with the leading county non-league side, Boston United, invited to join the three league teams.

In their first season in the competition they would defeat Grimsby Town in the semi-final before going on to lift the trophy with victory over Scunthorpe United in the final.

Boston's demotion from the Southern Football League at the end of the 1960–61 season saw them replaced by Gainsborough Trinity for the 1961–62 competition.

In the 1956–57 season, Scunthorpe United beat Lincoln City at Scunthorpe on 1 October 1956 in the first semi-final with a goal by Jones, and Boston United beat Grimsby Town 2–0 in the second semi-final with goals by Bloomer (2), on 16 October 1956.

Sharpe scored for Scunthorpe United, and the Boston goals were from Clarke, Dunn and Bushby (o.g.).

The Senior 'A' Cup was only played for once in this timeframe, Gainsborough Trinity defeating Boston United 2–1 in a replay on 15 April 1964.

The Northern Premier League was founded in 1968 with Boston United and Gainsborough Trinity as founder members.

[35] In 1969–70, Lincoln City reached the final by beating Grantham 5–1 away and Gainsborough Trinity 3–0 at home after a 3–3 draw away.

The 1983–84 competition was played as a straight knock-out between the six competing clubs, the league sides Grimsby Town, Lincoln City and Scunthorpe United and the three senior non-league sides Boston United, Gainsborough Trinity and Grantham.

Lincoln United's rise up the non-league pyramid saw them enter the competition in 1996–97 (they won the Lincolnshire Senior 'A' Cup in 1995–96).

Scunthorpe United ended Grimsby Town's five-year reign as champions, defeating them 5–4 on penalties in the 1996–97 final.

The 2008–09 competition was reduced to just the three Football League sides with Grimsby Town defeating Lincoln City in a semi-final tie before losing to Scunthorpe United in the final.

Boston and Gainsborough would compete for a place in the semi-final while the other three sides would automatically be entered with the winner of that match.

However the final despite always being a traditional pre-season event was now moved to October, with the semi-finals taking part in early August.

The table summarises the winners of the Lincolnshire Senior County Cup (1934–) and its previous names (1881–1934).