O'Regan's Longshots: A feast of weekend football outsider bets
Fri, 29 Aug 2025
Fri, 29 Aug 2025
Expert football tipster Matthew O'Regan is back with his latest outsider football betting tips column for Odds Now, covering matches across the UK.
Non-league football takes centre stage this week, with a juicy-looking slate from Steps 1 and 2 from the non-league pyramid.
There are also three goal-based angles covered in the Championship. So let's start with the action in the second tier.
Norwich have made a stuttering start to the season, suffering back-to-back 2-1 home defeats against Millwall and Middlesbrough. Away from Carrow Road, however, they’ve fared better, recording 2-1 wins at Portsmouth in the league and Watford in the cup.
Both teams have scored in four of Norwich’s five matches across all competitions, including all three of their league fixtures.
They now face Blackburn, who sit just above them on goal difference. Rovers have also had a mixed start, opening with a 1-0 defeat away to West Brom before falling 2-1 at home to Birmingham, conceding twice late on. They bounced back in style with a convincing 3-0 win at Hull.
It should be another entertaining game and I expect Norwich to win on their travels again.
Despite backing Millwall to win to nil last week, this time I’m siding with Millwall to win and Both Teams to Score at home to Wrexham. It’s a market that has already landed for the Lions in their league trip to Norwich and in their cup clash with Coventry.
Wrexham, meanwhile, are still searching for their first league win. They’ve lost 2-1 to Southampton, 3-2 to West Brom, and squandered a two-goal lead in a 2-2 draw with Sheffield Wednesday.
Cup matches have followed the same trend: a 3-3 draw with Hull and a 3-2 win over Preston. Remarkably, all five of their games in league and cup have seen Both Teams to Score and go over the goals line.
With Millwall boasting strong attacking options but weakened at the back following the sale of Japhet Tanganga, another high-scoring encounter looks likely. The hosts should have enough to edge it, but Wrexham’s scoring form suggests they’ll play their part too.
Maybe it’s reactionary after watching Oxford get dismantled 6-0 by Brighton in the cup last night, but something feels off for the Yellows under Gary Rowett this season.
They’ve lost all three league games so far and sit second-bottom, starting with a 1-0 defeat at home to Portsmouth, followed by a 3-2 loss at Hull courtesy of a late Oli McBurnie strike, and then a 1-0 defeat away at Birmingham – a game where the hosts could easily have scored more.
Coventry, by contrast, are unbeaten with two wins and a draw from their opening fixtures. The 0-0 at home to Hull was unusual for them, failing to convert any of their 18 chances and 1.43xG.
But they quickly bounced back, smashing Derby 5-3 before dismantling QPR 7-1. Lampard’s side look back to their free-flowing best, and against a fragile Oxford defence, they should have plenty of joy in front of goal once again.
This has all the makings of the weekend’s most entertaining clash, with two free-scoring sides meeting at in the North East.
Gateshead’s season has already been a rollercoaster: a 3-0 defeat at home to Southend, a 2-0 win at Eastleigh, then a heavy 4-0 loss at Rochdale before bouncing back with consecutive victories – 2-1 over Tamworth and a dramatic 4-3 win at Yeovil, where they overturned a 3-0 half-time deficit.
Aldershot’s campaign has followed a similar theme of goals. They opened with back-to-back-to-back 3-2 defeats, but since then have found their stride, thrashing Solihull Moors 5-1 and dismantling Morecambe 4-0.
This exact fixture ended 2-2 last season, and with both teams showing attacking firepower and defensive vulnerabilities – and a similarly high-scoring encounter looks likely.
One player who stands out in the markets is Ryan Hill. Already joint second-top scorer in the league with four goals, and on penalty duty, he looks great value to find the net.
AFC Fylde have been perennial contenders in the National League North, never finishing below third during their time in the division. They look set for another strong campaign, too, winning four of their opening five matches thus far.
Interestingly, all four victories have come with Fylde conceding, while their only defeat was a 2-1 loss to Scarborough – meaning Both Teams to Score has landed in all five games.
They now host newly promoted Bedford, who have found life tougher at this level but sit just above the drop zone. Bedford began with a 2-2 draw at Alfreton and have since lost three of their last four, though they’ve scored in every outing.
Their sole win came against Telford, a 3-1 success, ensuring BTTS has also landed in all five of their matches.
Scarborough have started the season strongly and sit fouth in the table despite a narrow 1-0 defeat at Kidderminster on opening day. Since then, they’ve gone unbeaten, beating AFC Fylde 2-1, drawing 2-2 away at a strong Chorley side before recording back-to-back 3-1 victories over Peterborough Sports and Merthyr Town.
They now welcome a struggling Southport outfit, who have lost four of their first five matches. Their only win came in a 3-1 success against Bedford, but otherwise it’s been tough going – losing 2-0 at Merthyr, 2-1 at home to Macclesfield, 2-0 at Worksop and 3-2 at home to Fylde.
With Southport’s defensive fragilities and Scarborough looking sharp in front of goal, an early breakthrough for the hosts could see the floodgates open.
The Tudors finished last season brilliantly under Lee Allinson on their own patch and have carried that form into this campaign, drawing 1-1 with Maidstone and beating Dorking 2-0. Their only defeat so far was a narrow 2-1 at Dagenham & Redbridge, in a game where they were undone by poor officiating.
They now host a Torquay side who have started the season strongly, winning both home games with three goals in each. But, as last year, it’s their away form that raises questions.
They’ve already drawn 1-1 at Maidstone and lost 2-1 at Horsham. Notably, both teams to score has landed in all five of their games so far.
Given Hemel’s strong home record and Torquay’s tendency to concede on the road, Hemel Hempstead to win with Both Teams to Score looks a big price.
I backed Hornchurch at 40/1 to win the title before the season, and the Urchins have made a flying start, collecting 13 points from their opening five games.
They began with four straight victories — 3-2 against Weston-super-Mare, 2-1 away at Eastbourne, 1-0 against Enfield, and 3-1 on the road at Farnborough — before sharing the spoils in a 3-3 thriller at Salisbury.
Both teams to score has landed in four of those five fixtures, with the exception coming at Enfield, who themselves have managed just one goal all season.
Next up, Hornchurch host a Chippenham side sitting just outside the relegation zone. Despite their league position, Chippenham have also been lively going forward, finding the net in every match bar their trip to Ebbsfleet.
Worthing host Maidstone in a repeat of last season’s National League South playoff quarter-final, a tie in which Maidstone triumphed 2-0.
The Rebels have reached the playoffs in all three of their National League South seasons, but after a slow start this year, climbing that same mountain looks increasingly difficult.
Known for free-flowing attacking football, Chris Agutter’s side have struggled this season following a change in formation. Agguter has favoured a back five, with inverted full-backs bolstering midfield and long balls targeted at Temi Babaola, who has yet to prove clinical in front of goal.
Worthing started the campaign with a 1-1 draw at home to Bath before a thrilling 4-3 away victory at Horsham. Since then, though, they have suffered 1-0 defeats at Chippenham and Farnborough, as well as a goalless draw at home to Enfield, leaving them without a goal in their last three matches against sides in 19th, 20th, and bottom place.
Maidstone, by contrast, remain unbeaten, conceding just twice in five games. However, they have lacked cohesion in attack, scoring only five times. Their results include 1-1 draws with Torquay and Hemel Hempstead, a 0-0 stalemate at Chelmsford, and wins over Hampton & Richmond (2-0) and AFC Totton (1-0).
Under 2.5 goals has featured prominently this season, landing in four of Worthing’s five games and in all five of Maidstone’s fixtures.
Meanwhile, Slough and Enfield have endured difficult starts. Slough’s five games have produced just seven goals, with all matches finishing under 2.5 goals.
Slough have scored only three and conceded four in their five matches, while Enfield have taken just two points from five games. Their last four games have all ended under 2.5 goals and under 1.5 goals, including two 0-0 draws and consecutive 1-0 defeats at home following a 3-1 opening loss to Torquay.
1.5 pts - AFC Fylde vs Bedford Town – Fylde win and BTTS – 12/5
1 pt - Gateshead vs Aldershot - 2+ goals each side - 3/1
1 pt - Gateshead vs Aldershot - Ryan Hill to score anytime - 9/2
1 pt - Scarborough vs Southport – Scarborough over 2.5 goals – 11/4
1 pt - Hornchurch vs Chippenham – Hornchurch win and BTTS – 5/2
1 pt - Worthing vs Maidstone and Slough vs Enfield - under 2.5 goals double - 12/5
0.5 pts - Norwich vs Blackburn – Norwich and BTTS – 5/1
0.5 pts - Millwall vs Wrexham – Millwall and BTTS – 4.33/1
0.5 pts - Coventry over 2.5 goals vs Oxford - 3/1
0.5 pts - Coventry over 3.5 goals vs Oxford - 9/1
0.5 pts - Hemel Hempstead vs Torquay – Hemel win and BTTS – 7/1
0.5 pts - Worthing vs Maidstone and Slough vs Enfield - under 1.5 goals double - 11/1
0.5 pts - Worthing vs Maidstone and Slough vs Enfield - under 0.5 goals double - 72/1
Total staked - 10 pts
Despite only being in his early 20s, Matthew O'Regan has wasted little time making a name for himself as a sound footballing judge.
With a strong social media following, gained as a result of his uncanny ability to repeatedly land big-priced winners, Matthew now shares his insights on the beautiful game – and how to profit on it – as his profession.
He credits most of his betting skill to working in a bookmaker shop as a youngster, seeing the silly mistakes most punters make which inspired him to try and attack things from a different angle.
When he's not scouring markets and writing columns, Matthew follows Brighton and his local non-league club Worthing.
Despite only being in his early 20s, Matthew O'Regan has wasted little time making a name for himself as a sound footballing judge.
With a strong social media following, gained as a result of his uncanny ability to repeatedly land big-priced winners, Matthew now shares his insights on the beautiful game – and how to profit on it – as his profession.
He credits most of his betting skill to working in a bookmaker shop as a youngster, seeing the silly mistakes most punters make which inspired him to try and attack things from a different angle.
When he's not scouring markets and writing columns, Matthew follows Brighton and his local non-league club Worthing.
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