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Hi.

If someones hold Tier 2 dependent visa for 3 years and then he/she holds 2 years skilled worker visa. Can he/she apply for ILR after 5 years of duration?

Can he/she apply for ILR after 5 years of duration?

No. You cannot combine dependent time with main tier 2 time to make up 5 years for ILR. Switching to main tier 2 migrant resets the clock to zero and a new 5 year period before ILR can be applied for.