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I will soon be applying for ILR at the end of my 5 year on Tier-1, but am not sure if my wife can apply together.
She is on her 4th year of her own Tier-1 currently. Earlier to her Tier-1 she got two previous entry clearances as Tier-1-dependant and Work-permit holder with gaps only due to travel and visa application time.

eyeLaar wrote:I will soon be applying for ILR at the end of my 5 year on Tier-1, but am not sure if my wife can apply together.
She is on her 4th year of her own Tier-1 currently. Earlier to her Tier-1 she got two previous entry clearances as Tier-1-dependant and Work-permit holder with gaps only due to travel and visa application time.

First answer No. Because she has to be dependent at time of application as your dependent.

But, does she have a continuous 5 years as work Permit and tier 1? If yes, she could be eligible independently.

No, she switched from Work permit to Tier-1-dependant and then onto Tier-1.
I thought indefinite leave is a category where people "settle". And given the "dependants" require just 2 years to prove the marriage to be allowed to "settle", am surprised on the restriction put over the "route".

I know that discretion is used in cases that are not straight forward, but given the fee is non-refundable, is it worth applying?

Your wife cannot apply with you as your dependent because she currently not your dependent.