In the show, the character was romantically involved with Izzy Armstrong (Cherylee Houston), Alya Nazir (Sair Khan) and Sarah Platt (Tina O'Brien).

The character was also engaged in feuds with Sarah's brother David Platt (Jack P Shephard), Izzy's father Owen Armstrong (Ian Puleston-Davies), and most prominently, with Anna's rapist Pat Phelan (Connor McIntyre).

Gary's story-lines include his conflict with PTSD after joining the army, forming a business partnership with Owen, bonding with his parents' adopted daughter Faye (Ellie Leach), a brief custody battle against ex-girlfriend Tina McIntyre (Michelle Keegan) after she becomes their surrogate and gives birth to Gary and Izzy's son Jake, a close friendship with Faye's biological father Tim Metcalfe (Joe Duttine), helping Sarah's daughter Bethany (Lucy Fallon) overcome her troubles with bullying in school and being subjugated to child grooming and sexual exploitation by her pimp Nathan Curtis (Christopher Harper), a one-night stand with Phelan's daughter Nicola Rubinstein (Nicola Thorp), which results in her giving birth to their son Zack and appointing Faye's boyfriend Seb Franklin (Harry Visinoni) to become his apprentice.

In 2019, Gary became the show's main antagonist when he was revealed to be the culprit who caused the death of Alya's sister-in-law, Rana Habeeb (Bhavna Limbachia), by sabotaging the Underworld Factory roof in his attempt to sort out his debts to loan shark Rick Neelan (Greg Wood).

Soon afterwards, Gary proceeded to establish a relationship with David's colleague Maria Connor (Samia Longchambon), clash with Rana's brother Imran Habeeb (Charlie De Melo) over the circumstances behind his sister's death, become enemies with ex-girlfriend Sarah's boyfriend Adam Barlow (Sam Robertson) after growing jealous of their newfound romance, develop a feud with Maria's love interest Ali Neeson (James Burrows), hospitalise Ali's brother Ryan (Ryan Prescott) after beating him up for unintentionally stealing his money and blackmail his own client Derek Milligan (Craige Els) into taking part in his scheme to invest the factory - which ultimately sparked the event of Derek instigating a lethal Christmas siege that culminates in his own death, though not after accidentally killing Ali's stepfather Robert Preston (Tristan Gemmill) and shooting David's wife Shona Platt (Julia Goulding) in the resulting impact.

Shortly afterward, Gary and Len steal and burn out a sports car that Joe's stepson David Platt (Jack P. Shepherd) and his friend Graeme Proctor (Craig Gazey) had been driving.

During an altercation, Gary mentions several things from David's past, including him driving into the lake in an attempt to commit suicide and accidentally pushing his mother Gail Platt (Helen Worth) down the stairs.

Things escalate when David enters his house, having seen Tina approaching, Gary blocks him from shutting the door and tells him "Come out and fight me like a man or are you scared?"

However, the Windasses have since been shunned by the rest of the Street; when Gary goes to the corner shop, he is ignored by Tina and taunted by Minnie Chandra (Poppy Jhakra), although Molly Dobbs (Vicky Binns) is less judgmental.

Gary and his father, Eddie Windass (Steve Huison) are told to get out of the kebab shop by Tina and are later ridiculed by Janice Battersby (Vicky Entwistle) and Sean Tully (Antony Cotton).

Becky McDonald's (Katherine Kelly) half-sister Kylie Turner (Paula Lane) sets her sights on Gary and the two end up sleeping together in Mary Taylor's (Patti Clare) motor home.

An army officer visits Anna and Eddie in November 2010, informing them that Gary was involved in a roadside bomb and is severely injured whereas the other troops, including Quinny, had died as a result.

The chaotic aftermath of the street's tram crash on 6 December 2010 triggers Gary's post-traumatic stress disorder and he is forced to flee to his home where he breaks down in tears.

As Gary and Izzy continue to argue, Tina becomes convinced they won't make good parents, so she decides to name the baby Joe and keep him for herself.

A few days later in March 2014, Phelan reappears at Weatherfield and summons Gary and Owen without the rest of their family's knowledge, telling the duo how he plans to get revenge on them over the incident.

Phelan assures Gary and Owen that he has further copies and then demands that either they complete the work for a minimum wage — gleaning no profit — or he would hand the CCTV footage into the police.

Whilst working there, Gary befriends David's niece Bethany Platt (Lucy Fallon) after she collapses as a result of taking diet pills that she purchased from the internet.

Gary soon learns that David is to blame for Anna's predicament when Bethany's mother, Sarah (Tina O'Brien), privately tells him the truth about the incident.

The couple and David soon work together with the latter's new girlfriend, Shona Ramsey (Julia Goulding), to imprison her ex-boyfriend Nathan Curtis (Christopher Harper) after learning that he has been sexually grooming and exploiting Bethany into his pimp business.

They are eventually successful when Nathan and his conspirators, including corrupt policeman Neil Clifton (Ben Cartwright) and fellow accomplice Ian Yardley (Anthony Bowers), are all found guilty of raping Bethany and receive maximum prison sentences.

Despite this, they continue to clash as Phelan sparks the events of Jason leaving Weatherfield for Thailand by sabotaging his business empire and later usurping his position as the landlord of a flat.

This escalates when Phelan defrauds Sarah, along with Alya's grandmother Yasmeen Nazir (Shelley King) and her friend Rita Sullivan (Barbara Knox), in his flats scam project called "Calcutta Street" — which culminates with Phelan causing the death of Sarah's stepfather Michael Rodwell (Les Dennis) by watching him die of a heart attack without providing help.

As Gary helps Sarah and her family as they grieve over Michael's death, he finds himself having to embark on some dangerous jobs in Ukraine in order to repay some of his debts.

Despite his efforts to prove his mother's innocence, Anna is found guilty for Seb's accident and is sentenced to five years imprisonment; Gary misses the verdict after being mugged whilst he and Bethany's close friend, Craig Tinker (Colson Smith), attempt to stop her from working as a lap dancer.

With Phelan's crimes exposed and presumed dead following a showdown with Jason's mother Eileen (Sue Cleaver), whom he previously married back in January 2017, Gary is granted ownership of the yard and helps Faye collaborate with their friend Daniel Osbourne (Rob Mallard) planning to secure Anna's release from her false imprisonment.

While Sarah is left outraged at her brother's behavior, Gary grows concerned for David and is surprised to later find out that he had been raped by his new friend Josh Tucker (Ryan Clayton), and was suggesting from PTSD.

He manages to cover up his involvement in both Rana's death and Rick's murder, but this contributes to his aggressive behavior that results in Sarah ending their relationship.

The character of Gary was created as part of a new family unit that new producer Kim Crowther introduced to the soap opera, consisting of a mother, father, son and uncle.

[10] Grace Dent of The Guardian stated her love for the Windass family and of the character Gary, and she went on to describe him stating: "Gary Windass loves thieving cars, stealing tools from vans, spitting globs of phlegm between his front teeth and, at the mere hint of sunshine, strutting about with his top off wearing trakkie-beeees that cry out for a good boil wash.

[13] Whereas Simon Swift of Soaplife magazine commented on the fact that on first looks he couldn't help feeling that Gary and the rest of the clan are a bit too much like original neighbours-from-hell the Battersbys.