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The first cup is the blessing of the festival day, it's the kiddush cup. The second cup of wine occurs really at the beginning of the Passover liturgy itself, and that involves the singing of psalm 113. And then there's the third cup, the cup of blessing which involves the actual meal, the unleavened bread and so on. And then, before the fourth cup, you sing the great hil-el psalms: 114, 115, 116, 117 and 118. And having sung those psalms you proceed to the fourth cup which for all practical purposes is the climax of the Passover.

Scott seems confused :
The Haggadah that was current during Y'shua's time
was begun by Rav Hill-el I at 100 BCE
The Haggadah for the Pesach Seder was written down
by Rav Judah ha-Nassi in 200 CE
A careful review of the haggadah for Pesach reveals:
The first cup is the cup of Freedom
"I will take you out"
The second cup is the cup of Deliverance
"I will Deliver you"
In modern Messianic Pesachs the breaking of the Matzos
into the afikomen,
( Its Greek meaning can be understood as "that which is coming" )
is followed by the eating of the Lamb dinner
Which is followed by The third cup which is the cup of Redemption
"I will redeem you"
followed by the singing of the Hill-el Psalms
The fourth cup is the cup of Blessing or Thanksgiving which
"I will take you as my people" (Deut 6:6-7)
I expect to share as the Bride with the BrideGroom
at the wedding feast of the Lamb
as outlined in Matthew 26:29

Thank you for allowing me share this with you.

b'shem Y'shua