The pair were teammates at Oakwell before Winnall's controversial move to Hillsborough in January.
Barnsley's Angus MacDonald in action (left)
Winnall has since made three appearances for Barnsley's bitter rivals but is yet to open his account, and was an unused substitute as the Owls beat Wigan Athletic on Friday.
The 26-year-old's place was instead taken by the Owls' latest recruit, Jordan Rhodes, and the former Middlesbrough man - whose 91 Championship goals since the start of 2012-13 are more than any other player has scored in that time - looks set to keep Winnall out of the side for Birmingham's visit this weekend.
With fellow frontmen Gary Hooper and Steven Fletcher soon to return from injury and suspension respectively, competition for a place in Wednesday's attack is arguably at its most fierce for some time.
And the situation is not lost on MacDonald.
When asked how he would approach Winnall when Wednesday travel to Oakwell later in the campaign, the Barnsley defender replied: "He would need to be on the pitch first."
He would need to be on the pitch first. https://t.co/IMhFNpdH7Y— Barnsley FC (@bfc_official) 8 February 2017
Fair play, Angus. Although we should perhaps point out that it was his own goal which set Wednesday on their way to a 2-0 win at Hillsborough last December.
Barnsley's Angus MacDonald deflect's Lucas Joao's header past his own 'keeper
Can Winnall succeed despite the presence of others at Hillsborough?