The England midfielder has complained of experiencing severe pain during the games against Bayer Leverkusen and Chelsea and Sir Bobby is anxious to have him available for the crunch Champions League tie at Inter next week.
Sir Bobby told Sky Sports: "Kieron is on fire - we can't stop him running - but he's had a further reaction and it's very painful.
"We don't know whether he can play two games anymore in a week. We'll have to look at it. Can he play an hour and do the damage to win us the match?''
Meanwhile Jermaine Jenas has resumed light training following his Achilles injury but is unlikely to be fit to face Boro.
But Laurent Robert is available again after suspension and Hugo Viana has suffered no reaction to his first match back, while Brian Kerr is expected to have recovered from his cold in time for Wednesday’s game.