Massimo Maccarone and Gaizka Mendieta both look set to seal departures from Middlesbrough before the transfer deadline closes on Wednesday.
Italian international Maccarone is Boro's club record signing after arriving for over £8 million - but despite becoming a cult hero with the fans, he is set to seal a return to Italy - with Siena looking set to win the race for his signature.
"Massimo is in talks at the moment with a couple of clubs in Italy and something may happen over the next 24 to 48 hours," said Boro boss Gareth Southgate.
"But there is nothing concrete as yet."
Maccarone's agent says a move to Siena is set to be completed.
"We are awaiting one document from Middlesbrough for the deal to be completed," said Paolo Fabbri.
"It's unlikely to arrive today, but we hope that it arrives no later than Wednesday. Otherwise, the situation will be complicated - and Massimo would have to return to Middlesbrough.
"Massimo is currently at his house in Italy, waiting for the go-ahead to travel to Siena."
Southgate revealed that former Spanish international Mendieta was also looking at offers from elsewhere.
"With Mendieta, there are a couple of clubs he is having talks with and we will just have to see how that progresses over the next couple of days," he said.
The Boro boss admitted he was not looking likely to bring any more new faces into his squad before Wednesday, with South Korean Lee Dong-gook the only new arrival so far.
"It is unlikely," he said of any further deals. "Until it is finished you are never 100 per cent certain, but I said all along I would only add if I felt it was the quality that would improve us and if I thought we were getting it at the right price.
"Unfortunately, because it is such a limited time, a lot of the prices do get inflated.
"But I am very comfortable with the squad I have got.
"It has been easier for us because our results have picked up and we have not been panicked into having to do something.
"We can be realistic about our aims and our goals and not make short-term decisions that we would be left with in coming years, or which might impact on what we want to do in the summer."
Boro spokesman Dave Allan did confirm to the Hungarian media that the club were still pursuing West Brom's Zoltan Gera.
"At this time I can only say Middlesbrough have been doing their best to make West Bromwich allow Zoltan Gera to join us," Allen told Nemzeti Sport.
"Gareth Southgate would like to see the Hungarian play in his team, he considers him to be a valuable footballer who would be very useful for Boro, so we haven't given up on signing him."