Kilgallon lines up at left-back just 48 hours after completing a season-long loan move from North-East neighbours Sunderland, while Halliday starts on the right of midfield after moving from Livingston this summer.
Gordon Strachan has reshaped his midfield in the absence of Willo Flood, Kevin Thomson and Gary O'Neil, and Estonia international Tarmo Kink makes his first start on the left.
Kris Boyd partners Scott McDonald in attack, with 20-year-old Jason Steele continuing in goal.
MIDDLESBROUGH (4-4-2): Steele; Bates, Wheater, McManus, Kilgallon; Halliday, Bailey, Robson, Kink; McDonald, Boyd.
Subs: Coyne (gk), Hoyte, Taylor, Arca, L Williams, Miller, Lita.
SHEFF UTD (4-4-2): Simonsen; Nosworthy, Morgan, Ertl, Bartley; Ward, Montgomery, Britton, Taylor; Evans, Cresswell.
Subs: Aksalu (gk), Bogdanovic, Yeates, Kozluk, Quinn, James, Chappell.