[1] Cummings was easily re-elected in the provincial election of 1990,[4] in which the Progressive Conservatives won a majority of seats.
He retained this position until 1999, when Filmon's Tories were defeated by the NDP under Gary Doer in a provincial election.
[1] Cummings retained his own seat in the 1999 election, defeating NDP candidate Louise Wilson[4] by 3871 votes to 3293.
In the 2003 election, he defeated NDP candidate John Harapiak by over 1400 votes,[4] despite the poor showing of the Progressive Conservative party elsewhere in the province.
In the buildup to this election, Cummings was a leading proponent of the PC party's plan to remove education taxes from residences and farmland.