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Boro must make home advantage count
Middlesbrough fans will have been disappointed to have missed out on automatic promotion this season, with the club having spent five non-consecutive weeks in second place throughout the course of the campaign. Unfortunately, the Teessiders' form dipped dramatically throughout March and continued into early April, causing them to drop out of the automatic spots.
Kim Hellberg has managed to arrest that slide, and they have ended the season strongly. They are unbeaten in four, winning each of their last two home matches and picking up points at fellow high-fliers Ipswich and Wrexham.
Curiously, they have struggled in front of their home fans recently, although plenty of those poor performances have come against lower-ranked teams who made it their mission to sit deep and create a low block. This made it awkward for Boro to find a way through, and they missed countless opportunities against Charlton, Oxford and Portsmouth.
Despite this, they have been priced up as 2/13.00 second favourites for promotion, and they should have enough firepower to cause Southampton a few problems this weekend.
Saints are unlikely to approach the game in the same way as many bottom-half dwellers, and this game should be fairly open, something which should suit the hosts. Hayden Hackney's participation is doubtful, although the influential midfielder could make his return for Tuesday's trip to Hampshire.
Nevertheless, Hellberg has options with both Riley McGree and Alan Browne able to sit alongside Aidan Morris in the centre of the park.
Eckert's side will look to bring their big game experience
Tonda Eckert was appointed on 5 December 2025, following the disappointing tenure of Will Still. Some fans were sceptical of his appointment, yet the German has not looked out of place and has been linked with Bundesliga vacancies recently.
Southampton have collected 56 points since his role was confirmed, the joint-most in the division alongside Ipswich. They have picked up four more points than Coventry, who were crowned champions just a couple of weeks ago.
Eckert has also taken this group of players to an FA Cup semi-final, where they were eight minutes away from forcing extra time against Manchester City. That experience will be handy over the next couple of weeks, and several squad members, including Taylor Harwood-Bellis, Ryan Manning and Flynn Downes, were also involved in the club's successful 2024 play-off campaign.
Interestingly, Eckert opted for a different approach against Premier League opposition, with the Saints soaking up pressure and hitting their opponents quickly and decisively on the break. He may look to replicate that approach here, given that Boro should have plenty of the ball in this first leg.
It won't be an easy 90 minutes for the visitors, but they should have enough experience and options from the bench to take at least a draw back to St. Marys for Monday night's re-match.
Back Southampton Draw No Bet
Don't expect either side to keep a clean sheet
First legs are traditionally cagey. Although last season bucked this trend considerably, Boro's last appearance in the play-offs saw them draw 0-0 with Coventry before losing the second leg by a single goal. In addition, Southampton drew 0-0 with West Brom in a forgettable first leg at the Hawthorns two seasons ago. This one is not expected to follow suit.
Southampton's away games have averaged 3.52 goals per game, and they haven't kept a clean sheet on the road since January 31st. They've also only failed to net in one away game all season - a 4-0 loss here at the Riverside at the beginning of 2026.
Boro have netted 10 times in their last four games and have scored nine goals when hosting the top four teams this season. Neither side has looked particularly dependable at the back, and they look less assured with former Middlesbrough man Nathan Wood deputising for Jack Stephens.
Whittaker and Azaz are the players to focus on
Boro's return to form has coincided with the return of Morgan Whittaker. The former Plymouth man has been the catalyst for improved performances, and he has netted three times in his last four appearances.
He wasn't at his best against Wrexham, yet he has managed two shots on target in each of his last two appearances at the Riverside.
Finn Azaz is likely to get plenty of abuse from the home fans, yet that may be the fuel that he requires to damage his former employers' hopes of promotion. He's had a fantastic season on the south coast with eight goals and 11 assists, and he also netted against Manchester City in the FA Cup. He came off the bench against PNE on the final day, but with a rare week off, he is likely to be one of the first names on the teamsheet.
Back Finn Azaz to Score or Assist
Back Morgan Whittaker to Score or Assist