Dele is out with a hamstring problem, while Winks twisted an ankle in yesterday's 1-0 win over Crystal Palace.
Harry Kane admits his fitness will have to be managed in the coming weeks as Tottenham wrestle with a mounting injury list.
England host Germany at Wembley on Friday and then play Brazil at the same venue on 14 November.
England face friendly matches against Brazil and Germany over the next fortnight, with Tottenham's Dele Alli having already pulled out of the squad due to injury.
"The hamstrings are fine but, look, we've got to keep an eye on it".
"I do everything I can when I play whether it's 90 minutes or 70 minutes, that's all I can do". "It's about maintaining it, it's a long old season so we go away now and we do a bit of work and hopefully get ready for Friday".
England have their first training session on Tuesday and Southgate, who has added the fit-again Michael Keane to his squad as an additional centre-half, will be desperately disappointed if either Kane or Winks, and possibly both, are forced to miss out. "It was a sore one", he said before it was announced he will withdraw from the squad.
It leave the England manager with a decision to make about whether he recalls Daniel Sturridge only a few days after going public to say the Liverpool striker could not expect to be involved when he was being used only sparingly for his club.
"I'm sure that the national teams all understand the situations of our players and they will help them to be fit for their next game here otherwise it will be very tough, with the Christmas period, tough for the players".
"I see myself as being a long-term England player", Abraham said.
But Kieran Trippier, Eric Dier and Danny Rose should all feature and for Kane, who is expected to captain England in at least one of the matches, that is a great source of pride. "Gareth will make the decision based on what he thinks is best for the players and the team".