He moved to MIddlesbrough for £15 million in July, 2017.
Doncaster Rovers travel to Preston North End, while both Sheffield clubs have been drawn at home.
Hull have not gone any further than the fifth round of the FA Cup since they reached the final in the 2013/14 season when they lost 3-2 to Arsenal after extra time.
However, earlier that season Pompey did win 2-0 at Carrow Road when a goal from Dave Kitson in the 73rd minute and a late penalty from Greg Halford, after Leon Barnett was sent off, sealed the win in Norfolk.
Marcelo Bielsa will get his first taste of the FA Cup Cup with Leeds, 20, and Daniel Farke's second-tier leaders Norwich, 28, will be hoping to transform their superb league form over into the cup.
Arsenal could play minor league side Solihull Moors in the FA Cup third round while London neighbours Tottenham Hotspur may face fellow minnows Southport after Monday's third round draw.