The two played alongside each other during the second half of last season after Cummings joined on loan from Nottingham Forest.
The ex-Hibs star, who won the Scottish Cup at Easter Road in 2016, is well known for indulging in hi-jinks off the park, including challenging Scottish wrestler Grado to a fight in the canteen of Hibs’ training ground.
Talking to Simon Ferry as part of the Open Goal series, Windass was asked to retell a story of Cummings from their days together at Ibrox.
He said: “I was with him once in Dubai. I’m with his agent, Cummings and Wes [Foderingham]. I think Graham Dorrans was there as well.
“He gets up, telling everyone ‘watch the Guccis, watch the Guccis’.
“He gets his steak, throws it up in the air and tries to volley it. The steak lands on the floor and he points at me and says, ‘that’s why you play ahead of me’.
“So he picks the steak up, puts it back on the fork, tries it again and volleys the steak across the restaurant.
“There’s a geezer having dinner with his misses, and it hits his chair here [just above the shoulder]. There was a big brown stain where it had landed.
“Everyone has just gone silent in the restaurant. He’s just like ‘sorry, sorry, sorry’.
“Everyone was p***ing themselves. I’m like oh my god, you’re a maniac.”
Cummings returned to Forest in the summer before moving on loan to Peterborough. Windass was sold by Rangers on the final day of the English transfer window, joining Wigan in a £2.5 million move.