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In corinthians Paul speaks repeatedly of winning the lost. If men are determined by God to be elect or not, how does the word win carry the sense of a contest be true. It seems to imply that the outcome is not determined.
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Within the context of 1 Corinthians 9:19-22, which is what I believe is in question, to win is as to win over, or as the KJV uses "gain" as in adding to your number.
I would add by way of explanation that although one is elect, they are still unknown by fellow men, and are yet called inwardly and outwardly in time. So with in the confines of human time we see persons brought out of the kingdom of darkness and into the Kingdom of God. They have been "won" over.
WCF
Chapter XI Of Justification
section 4
God did, from all eternity, decree to justify all the elect, and Christ did, in the fulness of time, die for their sins, and rise again for their justification:[b:34c138647d]nevertheless, they are not justified, until the Holy Spirit doth, in due time, actually apply Christ unto them.[/b:34c138647d]
Through what means then is the Holy Spirit usually applied?
Preaching and Evangelism.
Romans 10: 13-15
13 For "whoever calls on the name of the Lord shall be saved." 14 How then shall they call on Him in whom they have not believed? And how shall they believe in Him of whom they have not heard? And how shall they hear without a preacher? 15 And how shall they preach unless they are sent? As it is written: "How beautiful are the feet of those who preach the gospel of peace, Who bring glad tidings of good things!"
Hope this helps