Well-motivated electroweak dark matter is often hosted by an extended electroweak sector which also contains new lepton pairs with masses near the weak scale. In this paper, we explore such electroweak dark matter via combining dark matter direct detections and high-luminosity LHC probes of new lepton pairs. Using $Z$- and $W$-associated electroweak processes with two or three lepton final states, we show that dependent on the overall coupling constant, dark matter mass up to $170-210$ GeV can be excluded at $2sigma$ level and up to $175-205$ GeV can be discovered at $5sigma$ level at the 14 TeV LHC with integrated luminosities 300 fb$^{-1}$ and 3000 fb$^{-1}$, respectively.
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