Yes - January 2008 transfer window saw Spurs re-sign Defoe and Keane plus about 3 other first team squad players.
Moving back to January's transfer window, my guess would be Kessie being brought in as a CM from AC Milan as his contract ends in June 2022, so fee is low and we know Spurs have continued to work on Vlahovic (striker) who would certainly fill a gap and maybe a 3rd player coming in.
We'd need to sell at least 2 overseas trained players - Doherty would be the obvious one, but I wonder if Lo Celso's time at Spurs might be coming to an end as he has rarely impressed at Spurs - and with Kessie coming in I doubt if Lo Celso would get any playing time.
If we could identify a suitable HG player who is available, maybe Winks would move on, but not sure who the incoming HG player would be