Bootle by-election, May 1990

The first by-election was caused by the death of Labour Party Member of Parliament for Bootle Allan Roberts, on 21 March 1990. Roberts had held the seat since the 1979 general election, and his majority had remained over 15,000 even in the Conservative landslide victory of 1983. At the 1987 general election, his majority had increased to almost 25,000.

For the by-election Labour selected Michael Carr, a full-time official for the Transport and General Workers Union, and a former Labour councillor. The Conservatives, who had consistently taken second place in the seat, but were struggling in the national polls, nominated James Clappison, a barrister from Yorkshire. He had unsuccessfully contested Barnsley East for the party in 1987, and the South Yorkshire constituency at the 1989 European Parliament election.

The newly named Liberal Democrats had suffered in the national polls since their formation by a merger of the Liberal Party and the Social Democratic Party, and in Bootle they were challenged by both David Owen's continuing Social Democratic Party and Michael Meadowcroft's continuing Liberal Party, both consisting of members of the former parties who had rejected the merger.

The Green Party also stood a candidate. Screaming Lord Sutch of the Official Monster Raving Loony Party and an independent rounded out the field.

The Loonies gained publicity after the Labour Party election agent unsuccessfully tried to get Sutch charged with having a public house as an election campaign headquarters. This had not been illegal since 1987.

Bootle by-election, May 1990

Party		Candidate	Votes	%	±%
	Labour	Michael Carr	26,737	75.4	+ 8.5
	Conservative	James Clappison	3,220	9.1	− 11.0
	Liberal Democrat	John Cunningham	3,179	8.9	− 4.1
	Green	Sean Brady	1,269	3.6	N/A
	Liberal	Kevin White	474	1.3	N/A
	Monster Raving Loony	Lord David Sutch	418	1.2	N/A
	Social Democrat	Jack Holmes	155	0.4	N/A
	Independent	T. J. Schofield	27	0.1	N/A
Majority			23,517	66.3
Turnout			35,477	50.6
	Labour hold		Swing	+ 9.7

The election was held on 24 May. Despite having to contend with a large field of candidates, Carr increased the Labour vote, to win with more than three-quarters of all the votes cast. The Conservative vote halved, although they retained second position, as the Liberal Democrat vote could not match that of the SDP-Liberal Alliance in 1987. The Greens polled 3.6%, while the continuing Liberals fared poorly, and the continuing Social Democrats were beaten even by the Monster Raving Loonies. Sutch jokingly offered to form a coalition with them, and the party was wound up soon afterwards, but Holmes formed yet another Social Democratic Party of members who wished to continue.

Carr died in July of that year and a second by-election was held.