Portsmouth to face Brighton in Carabao Cup second round - Derby or Preston await winners in next stage
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Kenny Jackett's side scraped past Stevenage in the opening round last month.
Pompey were given an almighty scare against the League Two outfit at Broadhall Way, though.
The visitors found themselves two goals behind after 10 minutes and then 3-1 down within the half-hour.
Yet strikes from Ronan Curtis, Gareth Evans and John Marquis ensured the Blues drew 3-3 after 90 minutes and took the tie to penalties.
Craig MacGillivray – who replaced Alex Bass at half-time against Boro – made three penalty saves as the Blues won the shootout 3-1.
And Pompey have been rewarded with a clash against Brighton for their triumph.
That means there will be a reunion with Blues academy graduate Adam Webster, who joined the Seagulls for £20m from Bristol City last summer.
Jackett’s side also took on Brighton earlier this summer in a behind-closed-doors pre-season friendly, with Pompey losing 3-0.
The Blues will make the short jaunt across the A27 on either Tuesday, September 15 or Wednesday, September 16.
The last competitive meeting between the south-coast sides came during the 2011-12 season when both were in the Championship.
If Pompey do deliver an unlikely victory at the Amex Stadium then they will go to the winners of Derby and Preston’s all-Championship clash.
Former Fratton favourite Matt Clarke is on loan at Derby from Brighton.
Last season, the Blues reached the third round before crashing out to bitter rivals Southampton.