The Montreal Canadiens have the most series wins by a team in the Stanley Cup Finals, with 23 wins.

which team has won the most stanley cups
CanadiensSt. PatricksRed WingsBlackhawksBruinsPenguinsOilersIslandersRangersLightningDevilsSenatorsAvalancheKingsFlyersMaroonsMetropolitansDucksHurricanesCapitalsFlames231311665544333222221111
TEAMSERIESGPSERIES WWLTOTLPTSPTS%GGAPP%PK%S/GPSA/GP
Montreal CanadiensMontreal CanadiensStanley Cup Finals166231046110209.63048439515.083.531.4227.72
Toronto St. PatricksToronto St. PatricksStanley Cup Finals10513564900112.53327826933.0334.88
Detroit Red WingsDetroit Red WingsStanley Cup Finals12711616600122.48031631416.882.831.2428.56
Chicago BlackhawksChicago BlackhawksStanley Cup Finals71634370068.47918720511.678.630.0230.76
Boston BruinsBoston BruinsStanley Cup Finals98637583077.39323126517.285.229.1629.79
Pittsburgh PenguinsPittsburgh PenguinsStanley Cup Finals35522130044.6291018519.287.127.8330.03
Edmonton OilersEdmonton OilersStanley Cup Finals38523141047.61812710020.481.629.6625.76
New York IslandersNew York IslandersStanley Cup Finals2441770034.708997837.080.030.0430.46
New York RangersNew York RangersStanley Cup Finals55423320046.41812414615.287.129.3532.35
Tampa Bay LightningTampa Bay LightningStanley Cup Finals24314100028.583585021.085.528.2926.54
New Jersey DevilsNew Jersey DevilsStanley Cup Finals30317130034.567696312.281.727.6722.70
Ottawa SenatorsStanley Cup Finals163952020.6253727
Colorado AvalancheColorado AvalancheStanley Cup Finals112830016.727341519.288.625.8229.91
Los Angeles KingsLos Angeles KingsStanley Cup Finals162970018.563433318.888.931.3128.50
Philadelphia FlyersPhiladelphia FlyersStanley Cup Finals44216280032.36412814926.367.028.1430.91
Montreal MaroonsStanley Cup Finals122840016.6672612
Seattle MetropolitansStanley Cup Finals102541011.5503025
Anaheim DucksAnaheim DucksStanley Cup Finals121750014.583283013.284.823.8325.25
Carolina HurricanesCarolina HurricanesStanley Cup Finals121570010.417263016.288.623.6730.17
Washington CapitalsWashington CapitalsStanley Cup Finals9145008.444272721.280.026.1135.44
Calgary FlamesCalgary FlamesStanley Cup Finals1818100016.444464422.784.426.8326.28
Dallas StarsDallas StarsStanley Cup Finals29111180022.379699611.879.129.2831.21
St. Louis BluesSt. Louis BluesStanley Cup Finals191415008.21135655.670.825.8933.58
Victoria CougarsStanley Cup Finals8144008.5001918