Darkness would fall over the land [this was fulfilled on TWO continents!] (Amos 8:9); His hands, feet (Psalm 22:16) and side (Zechariah 12:10) would be pierced, but none of His bones would be broken (Psalm 34:20); His own people would reject Him (Isaiah 53:3) and hate Him without cause (Psalm 69:4); His friends would witness His ordeal from afar (Psalm 38:11); and people would cast lots for his clothing (Psalm 22:18).
McDowell notes that the Old Testament was completed in about 450 B.C. The Septuagint (Greek translation) was begun during the reign of Ptolemy Philadelphus (285-246 B.C.), which means the Hebrew version had to have been completed at least 250 years before Christ was born.
He also notes that while it's true that Jesus could have arranged to fulfill some of these prophecies, He could not have orchestrated the place, time and manner of His birth, that He would be betrayed, the manner of His death, people's reactions to His crucifixion, the piercings and the burial. The statistical odds that any man might have fulfilled all eight of those prophecies, let alone 61 (or 574) of them, are 1 in 10 to the 17th power, or 1 in 100,000,000,000,000,000.