The last 16 line-up is dominated by Premier League clubs, including the big guns of Arsenal, Manchester City, Manchester United, Chelsea and Liverpool along with a few other well-heeled teams besides.
It remains to be seen if any one of the Owls, Tigers and/or Boro are left standing by the time the quarter-final draw takes place. But here’s hoping.
The Owls welcome an in-form Arsenal, who visit Hillsborough for the first time since January 2000.
Hull City tackle another side who are in outstanding recent form in Claudio Ranieri’s Leicester City.
Boro, meanwhile, head to Old Trafford to face Manchester United - having enjoyed many famous cup battles with the red side of Manchester over the years.
Here’s a few historical facts and lowdowns on each tie.
SHEFFIELD WEDNESDAY v ARSENAL
Tonight’s tie evokes memories of the 1993 League Cup final, a game which saw Steve Morrow score the winner for the Gunners, but then famously broke his collarbone in the ensuing celebrations after being hoisted upon his shoulders by Arsenal captain Tony Adams following the final whistle.
In the same season, Wednesday took the Gunners to a replay in the FA Cup final, with Gunners defender Andy Linighan, complete with a broken nose, heading home a dramatic 119th-minute winner in a 2-1 win after extra time.
The pair have met four times in the League Cup, with the Gunners winning them all. Their last meeting came at Highbury in November 1995 when goals from Ian Wright (pen) and John Hartson gave the Gunners a 2-1 victory, with Marc Degryse scoring for the Owls.
The last League Cup meeting came in January 1988 when the Gunners prevailed 1-0 en route to the final, which they lost out 3-2 in a classic with Luton Town.
The pair’s cup history is also remembered for an epic FA Cup contest in the bleak winter of 1979.
The Owls and Arsenal famously locked horns in nine hours of third-round football which went to a fourth replay.
The first clash at a snowy Hillsborough ended 1-1 with Jeff Johnson cancelling out a strike from Mexborough-born Alan Sunderland.
Iin the Highbury replay, a late Liam Brady goal spared the Gunners blushes after the third-division Owls, managed by Jack Charlton, took the lead through Rodger Wylde.
In the second replay at Filbert Street, the Owls came from behind twice to draw 2-2 thanks to a Brian Hornsby double and the pair could not be separated in a third replay at the same venue in a 3-3 draw - Dave Rushbury, John Lowey and Hornsby (pen) netting for Wednesday.
A third contest ensued at Leicester, with goals from Steve Gatting and Frank Stapleton finally sending Arsenal through. The Gunners went onto lift the trophy in May after beating Manchester United 3-2.
HULL CITY v LEICESTER CITY
Hull City have never made it to the quarter-finals of the League Cup, having previously reached this stage in 1973-74, 1975-76, 1977-78 and 2013-14.
Steve Bruce is a previous winner, lifting the old Milk Cup while at Norwich in a 1-0 victory over Sunderland thirty years ago at Wembley in the spring of 1985, a game which saw him named man-of-the-match. He took Birmingham to the last eight in 2005-06.
Leicester have won the competition three times, famously lifting the competition after a replay at Hillsborough in 1997, with Steve Claridge’s extra-time goal seeing them beat Middlesbrough 1-0.
Hull are without a win in five matches against the Foxes, who triumphed 4-2 in their last League Cup meeting in East Yorkshire in September 2002.
Leicester scored three goals in extra-time to power past brave Hull, after the game had been level at 1-1 after 90 minutes.
The extra-half hour saw Paul Dickov, Alan Rogers and James Scowcroft net for Leicester, with Ian Ashbee firing a late concession.
In normal time, Rogers gave Leicester the lead after 17 minutes, but Gary Alexander levelled on the half-hour after converting debutant Richie Appleby’s free-kick.
Hull disposed of Leicester en route to the last 16 in 1973-74, beating the Midlanders 3-2 in a replay at Boothferry Park after the first tie ended deadlocked at 3-3. Hull bowed out to Liverpool in a round-four replay.
MANCHESTER UNITED v MIDDLESBROUGH
The pair have had some rare old cup ding-dongs over the years, memorably meeting in a two-legged League Cup semi-final in 1991-92.
After a goalless draw at Ayresome Park, United prevailed 2-1 after extra-time following a gripping second leg, breaking Boro’s hearts through a 106th-minute goal from teenage sensation Ryan Giggs.
Lee Sharpe put United in front just before the half-hour, but Bernie Slaven levelled.
It was a night when ex-Boro defender Gary Pallister cleared off his line to deny good friend Slaven, while Peter Schmeichel denied Willie Falconer with a stunning reaction save.
But United found a way, courtesy of Giggs’ strike - and beat Nottingham Forest 1-0 in the final.
Boro famously were the last time to win at Old Trafford during the Red Devils’ treble season of 1998-99, winning 3-2 just before Christmas.
During the current century, United have enjoyed the whip hand and are unbeaten in their last ten outings with the Teessiders.
The pair met in the League Cup in 1974-75, with United - then in the second division - beating Jack Charlton’s top-flight Boro 3-0 in a replay at Old Trafford after a 0-0 draw on Teesside. But Tommy Docherty’s bowed out to Norwich City in the last four.
Back in the early seventies, big cup encounters between United and Boro were commonplace.
In the 1969-70 campaign, an FA Cup sixth-round clash saw Boro draw 1-1 with United in front of 40,040 at Ayresome Park, John Hickton netting for the visitors nine minutes before the break to cancel out Carlo Sartori’s opener.
Back at Old Trafford, United went through thanks to a Willie Morgan penalty 12 minutes from time, four minutes after Hickton had restored parity after Bobby Charlton had fired the hosts in front - to set up a last four clash with Leeds.
The following season of 1970-71, Boro had their revenge, triumphing 2-1 in front of another sell-out of 40,040 on home soil, through goals from Hughie McIlmoyle and Derrick Downing in a third-round replay - after a 0-0 draw at Old Trafford.
The pair were again pitted together in the following season in 1971-72 when United strolled to a 3-0 fifth-round replay win at Ayresome Park through goals from Morgan (pen), George Best and Bobby Charlton following another goalless stalemate in Manchester.