The Watkins Glen International road course has been hosting NASCAR Cup Series races since 1986. However, 2020 was not one of them, as the series' annual stop at Upstate New York was shifted to the Daytona Road Course instead, due to COVID-19 restrictions.For the 2021 NASCAR season, Watkins Glen is back on the roster and will host one of seven scheduled road course races.Tony Stewart holds the record for the most wins at the Glen, having triumphed in 2002, 2004, 2005, 2007, and 2009. Jeff Gordon is second-best to Stewart with a total of four wins.With that in mind, let's take a look at each of his wins at Watkins Glen and how it came about.20022002 Sirius at the Glen (Watkins Glen). Tony Stewart claims a controversial victory just one week after punching a reporter at the Brickyard 400. Penske protested the win but the victory was upheld. His third victory of 2002 and 15th of his career. #2002NascarWinstonCupSeries pic.twitter.com/kTHjd4APT2— Nicholas Todd Smiley (@RonnysKid32) July 7, 2019Tony Stewart had a rather rough week in the lead-up to the race at Watkins Glen.He was involved in an altercation with a photographer post the Brickyard 400, which resulted in him being fined by NASCAR and also penalized with a 25-point deduction.Stewart qualified 3rd for the Sirius Satellite Radio at The Glen, and instead of being bogged down by past events, channelized his energy in leading 34 laps on his way to winning the race.This race wasn't free of controversy either as it was revealed that Stewart had jumped the restart. However, officials later upheld his win, marking his first of five wins at Watkins Glen.That same year, Tony Stewart also went on to win his first Winston Cup championship.You might also like: NASCAR Hall of Fame: Eligibility, Selection process, Induction, and Inductees20042004 Sirius at the Glen (Watkins Glen). Tony Stewart leads 46 laps and overcomes an upset stomach to grab the checkers. The win is Stewart’s second of 2004 and 19th of his career. #2004NascarNextelCupSeries pic.twitter.com/d1KOJTwXAR— Nicholas Todd Smiley (@RonnysKid32) May 29, 2020The win at the 2004 Sirius at The Glen didn't come easy either.Starting in the fourth position, Stewart battled a stomach bug as he persisted against Canadian road ringer Ron Fellows and eventually edged him off to claim victory.Unlike 2002, Stewart could not keep the form going as he finished sixth in the Cup points standings.2005Tony Stewart celebrating Sirius Satellite Radio At The Glen in 2005. Photo: Getty ImagesThe win in 2005 will go down as one of Tony Stewart's most dominant performances at Watkins Glen.The Sirius Satellite Radio at The Glen saw Stewart allow only three other drivers (Jeff Gordon, Robby Gordon, and Jimmie Johnson) to lead multiple laps as he himself led a total of 83 to win the race.The win was Stewart's No. 20 Chevrolet's fifth victory in seven races - Sonoma Raceway, Daytona International Speedway, New Hampshire Motor Speedway, and Indianapolis Motor Speedway were the other four wins - while setting the record for most laps led by a race winner.He also won his second Cup Series title at the end of the season.You might also like: How much money do NASCAR drivers make?2007Tony Stewart wins at Watkins Glen in 2007 to score 32nd career Cup win. #nascar #tbt pic.twitter.com/Lx4W5esiFl— Chevy48 (@chevychevelle48) August 3, 2017This win at Watkins Glen could be the easiest of the three mentioned above, but the fact that Tony Stewart applied enough pressure on Jeff Gordon to induce a mistake on him is a credit to Stewart's ability behind the wheel.Gordon was in the lead consistently after having started from pole and led 51 laps. However, a self-destructive spin on Turn 1 with just two laps to go allowed Stewart to get past and take the checkered flag at the Centurion Boats at The Glen.It was also his fourth career win on this road course.You might also like: Everything you need to know about the NASCAR Hall of Fame2009Tony Stewart wins Watkins Glen 2009 starting P13 leading 34 laps to score 36th career victory. #NASCAR #AlwaysRac14g pic.twitter.com/3O9jXwlPbx— Chevy48 (@chevychevelle48) November 17, 20162009 saw Tony Stewart make a move from Joe Gibbs Racing (JGR) to Haas CNC Racing where he took half ownership of the team to form Stewart-Haas Racing (SHR).Driving the No. 14 Chevrolet in the Heluva Good! Sour Cream Dips at The Glen, which saw delays due to rain, Stewart held off Marcos Ambrose on his way to a 36th career win and the fifth at Watkins Glen.You might also like: Top 5 fastest cars in NASCAR historyOther Drivers who have won at Watkins GlenBuck Baker- 1957Billy Wade- 1964Marvin Panch- 1965Tim Richmond- 1986Rusty Wallace- 1987, 1989Ricky Rudd- 1988, 1990Ernie Irvan- 1991Kyle Petty- 1992Mark Martin- 1993, 1994, 1995Geoff Bodine- 1996Jeff Gordon- 1997, 1998, 1999, 2001Steve Park- 2000Robby Gordon- 2003Kevin Harvick- 2006Kyle Busch- 2008, 2013Juan Pablo Montoya- 2010Marcos Ambrose- 2011, 2012AJ Allmendinger- 2014Joey Logano- 2015Denny Hamlin- 2016Martin Truex Jr- 2017Chase Elliott- 2018, 2019You might also like: How can NASCAR cars go so fast