The May 1990 Bootle by-election was held on 24 May 1990. It 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.