The artist, who is also Haines's wife, made several portraits of the ex-Auteurs singer-songwriter which were packaged with the limited edition release of Outsider Music Volumes 1-50 last year.
"To accompany Mr Luke Haines on his one and only Outsider Music concert at the Hoxton Pony, January 19 2011, Siân Superman (that is me, the wife) will be painting LIVE on stage," she confirmed on her official blog.
"30 golden minutes of Outsider Music - 30 treacherous, vodka-sodden, paint-splattered, 100% figurative minutes to paint a complete canvas artwork of Mr Haines' a-singin' and a-strummin'."
She added: "The painting will be raffled off/thrown into the baying crowd at the end of the evening."
Haines will play a complete set of songs from his Outsider Music project at the show, followed by a second performance of material from his back catalogue.