Morley-born Howson - who came through the ranks at the Whites academy - remains a strong fan favourite at Elland Road.
He was part of the League One-winning promotion side under Simon Grayson, spending six years in the senior ranks at his boyhood club before moving onto Norwich City and now Middlesbrough - where he has been since 2017.
Howson, among his 225 appearances, famously bagged the assist for Jermaine Beckford's winner at Old Trafford in 2010 - in one of the biggest shocks in FA Cup history.
Third division Leeds travelled across the Pennines to face arch rivals and reigning Premier League champions Manchester United only to stun their hosts and Sir Alex Ferguson 1-0 against the likes of Wayne Rooney.
On Friday night, Howson again made history at the Red Devils in English football's oldest and most famous competition.
The 33-year-old was this time part of a Middlesbrough side - which included ex Leeds players Sol Bamba and Lee Peltier - as they defeated Manchester United on penalties in the fourth round of the tournament.
Jadon Sancho opened the scoring for Ralf Rangnick’s star-studded side, but Boro's Matt Crooks levelled amid handball confusion and the match finished 1-1 after extra-time.
Every penalty found the net until Anthony Elanga struck his effort into the Stretford End, wrapping up an 8-7 spot-kick success for the Teessiders and sending the 9,500 visiting fans wild.
Howson, Bamba and Peltier all scored from the spot while the former was seen giving a fist pump to the Stretford End after finding the back of the net.