Barnsley made a winning start to their first game in this competition since winning the whole thing in its Johnstones Paint Trophy guise.
The Reds are now unbeaten in their last eight matches in the competition (W5 D3), and two of those draws went to a penalty shootout which Barnsley went on to win.
Prior to this run Barnsley had played six matches in this competition and won only one.
Indeed Oldham were the last team to eliminate Barnsley from this competition, winning 4-2 on penalties following a 2-2 draw at Boundary Park in the Johnstones Paint Trophy Northern Second Round in October 2014.
The Reds have now won each of their last five meetings with Oldham, with that JPT defeat the only one of the past eight meetings Barnsley have failed to win.
Barnsley have won three successive games at Boundary Park for the first time ever.
Barnsley have scored in each of their last 11 matches in this competition - a total of 21 goals - this after failing to score in their first four.
This was the first time Barnsley have come from 1-0 down to win a match in exactly 12months, last occurring in a 3-2 League Cup victory over Derby in September 2017.
It is the fourth time they have conceded first and come back to win in this competition.
This was the sixth game George Moncur has scored in for Barnsley and only the second they have gone on to win. Both of his goals so far in 2018-2019 have come in cup competitions.
Victor Adeboyejo meanwhile has scored in three matches this season and Barnsley have won them all.
In the first eight games of the season (all competitions) only Blackpool and AFC Wimbledon have managed to stop Barnsley from scoring at least twice.
They have scored at least twice in four successive matches for the first time since the final four games of 2015-2016 when they actually managed it in their final five matches.
Barnsley enjoyed 52% possession in this match, only at Bradford (49%) have they failed to have more ball possession than their opponents this season.
13. Jack Walton
6. Liam Lindsay
8. Cameron McGeehan
11. Lloyd Isgrove
14. Jared Bird
18. Adam Jackson
21. Mike Bahre
22. Jordan Williams
28. Ben Williams
29. Victor Adeboyejo
33. Jacob Brown.
Ethan Pinnock (for Lindsay 45)
Mamadou Thiam (for Isgrove 68)
George Moncur (for Bahre 73)
35. Jake Greatorex
37. Jasper Moon
38. Jordan Helliwell
39. Kieran Feeney
13. Zeus De La Paz, 3. Andy Taylor, 4. George Edmundson, 9. Sam Surridge, 14. Jonathan Benteke, 17. Christopher Missilou, 18. Sam Graham, 19. Callum Lang, 22. Johan Branger-Engone, 28. Mohamed Maouche, 34. Tom Hamer.
Jose Baxter (for Missilou 58)
Chris O’Grady (for Surridge 61)
Dan Gardner (for Lang 74)
43. Ewan McFarlane, 20. Jamie Stott, 23. Rob Hunt, 26. Peter Clarke.
Checkatrade Trophy results:
Tuesday 4th September 2018:
NORTHERN GROUP A
Carlisle United 2-3 Morecambe
Sunderland 0-0 Stoke City U21 (Sunderland win 4-2 on penalties)
SOUTHERN GROUP B
Colchester United 0-2 Southampton U21
Southend United 3-1 Cambridge United
SOUTHERN GROUP D
Yeovil Town 0-0 Exeter City (Exeter win 4-3 on penalties)
SOUTHERN GROUP E
Forest Green Rovers 4-0 Cheltenham Town
SOUTHERN GROUP F
Northampton Town 0-1 Wycombe Wanderers
Oxford United 3-0 Fulham U21
Spasov pen 86
SOUTHERN GROUP G
Charlton Athletic 2-2 AFC Wimbledon (Wimbledon win 4-2 on penalties)
SOUTHERN GROUP H
Luton Town 2-1 Brighton and Hove Albion U21
Milton Keynes Dons 3-3 Peterborough United (MK Dons win 6-5 on penalties)
NORTHERN GROUP B
Rochdale 2-1 Bury
Lavery pen 70
NORTHERN GROUP C
Macclesfield Town 3-3 Blackpool (Macclesfield win 5-3 on penalties)
Rose pen 78
NORTHERN GROUP D
Tranmere Rovers 3-4 Crewe Alexandra
NORTHERN GROUP E
Burton Albion 1-2 Walsall
NORTHERN GROUP F
Oldham Athletic 1-2 BARNSLEY
NORTHERN GROUP G
Doncaster Rovers 1-3 Newcastle United U21
Grimsby Town 2-1 Notts County
Rose pen 69
NORTHERN GROUP H
Lincoln City 1-2 Mansfield Town
Scunthorpe United 0-0 Wolverhampton Wanderers U21 (Scunthorpe win 4-2 on penalties)
SOUTHERN GROUP A
Crawley Town 1-1 Tottenham Hotspur U21 (Crawley win 5-3 on penalties)
Portsmouth 4-0 Gillingham
Pitman pen 55
Barnsley lie in 1st place in Checkatrade Trophy Northern Group F with 3 points from 1 game.
Up to 05/09/18
Sky Bet League One Matchday Seven: Barnsley v Walsall, Saturday 8th September 2018. Kick-Off: 3pm
On The Road:
Sky Bet League One Matchday Eight: Coventry City v Barnsley, Saturday 15th September 2018. Kick-Off: 3pm