An individual cannot be elected mayor without additionally winning an at-large city council seat.

Early Jordan Levy Independent The 1987 Worcester, Massachusetts mayoral election was held on November 3, 1987.

[11] Jordan Levy Independent Raymond Mariano Democratic The 1993 Worcester, Massachusetts mayoral election was held on November 2, 1993.

Ultimately the mayoral candidates on the ballot were John B. Anderson, Austin A. Heath, Konstantina Lukes, and Raymond Mariano.

There were enough candidates in the at-large city council in 1995 that a primary was mandated for it, which was held in mid-September.

[24] While running for mayoral reelection, Murray had already begun his campaign for the 2006 Massachusetts lieutenant gubernatorial nomination.

[10] It saw the reelection of incumbent mayor Konstantina B. Lukes, who had been appointed to the position earlier that year after Tim Murray resigned to become Lieutenant Governor of Massachusetts.

[24] Rather than issues, the election largely focused on the personality and the leadership style of Lukes.

[24] Rushton would ultimately receive most of the endorsements from major Democratic politicians in the region.

[24] Rushton's brother-in-law, Worcester County's new District Attorney Joseph D. Early, appeared at campaign events for him, marking the first time in decades that a District Attorney had involved himself in a political campaign.

[24] This field large enough that a primary was mandated for the at-large city council election, which was held in mid-September.

[24][31] These were Dennis L. Irish and Mike C. Perotto, who had respectively placed fifth and eighth out of all candidates in the at-large City Council primary.

[31] This bolstered the Democratic Party's hopes of coalescing opposition to Lukes around a single candidate, which had emerged to be Rushton.

[24] Rosen declared his candidacy after the at-large City Council primary,[24] in which he had placed first.

[31] Rosen's entrance into the race posed an obstacle to the Democratic Party leadership's hopes of coalescing opposition to Lukes behind a single candidate.

[32] The initial result, seeing Lukes lead by only 105 votes, was narrow enough that a hand-recount was conducted after Rushton requested one.

[10] It saw the election of Joseph C. O'Brien, who unseated incumbent mayor Konstantina B. Lukes.

[37] While there was speculation that Frederick C. Rushton, who had lost the 2007 to Lukes by an immensely narrow margin, might challenge her again in 2009,[43] he ruled it out in February 2009.

[45] Lukes, as she did in the previous election, saw two strong challengers, the two this time being O'Brien and Toomey.

[42] O'Brien's candidacy was supported by lieutenant governor and former Worcester mayor Tim Murray.

[46] Toomey was endorsed by the Worcester County Sheriff and one of the city's two state senators.

[42] O'Brien and Toomey criticized Lukes for being to inactive a mayor, and argued that she was ineffective at advocating for the city at the state and federal level.

[42] Lukes refuted accusations that she was too inactive, arguing that the role of mayor was not intended to be a full-time position.

[42] Lukes argued that she had independence from what she claimed was a Murray-McGovern run political machine.

[42] In an interview shortly after losing the election, Lukes would blame the "pro-retire, pro-union" vote for her loss.

O'Brien was the only non-incumbent individual elected to a citywide office in Worcester that year.

On September 16, 2011, incumbent mayor Joseph C. O'Brien announced that he would no longer be seeking reelection, citing family concerns.

[59] It saw the reelection of incumbent mayor Joseph Petty to a record sixth term.

Incumbent mayor Joseph Petty won re-election to a seventh term in office.

As the mayoral runner-up, King automatically became vice chair of the city council, taking over from Colorio, who won the position in the 2021 election.