In a scene that mingled romance with the competitive spirit of golf, Vanessa Trump and Tiger Woods were spotted enjoying a tender moment before Woods faced a challenging return to the greens. The golf legend made his much-anticipated comeback at The Golf League event on Tuesday night in Palm Beach.

Amidst the crowd was Trump, supporting Woods as he participated in his first tournament since 2024. Unfortunately for Woods, the evening did not unfold as hoped. His team, Jupiter Links GC, fell short in the finals of the league’s second season, marking a disappointing night for the 15-time major champion.

Among the spectators was Vanessa Trump, known for her past connection to former President Donald Trump, accompanied by her teenage daughter, Kai. Notably, tennis superstar Serena Williams was present too, cheering for her team co-owned with her husband, Alexis Ohanian, daughter Olympia, and sister Venus.

During the decisive match of the TGL finals, Jupiter Links faced a formidable opponent in the Los Angeles Golf Club at the SoFi Center in Florida. Woods, alongside teammates Tom Kim and Max Homa, suffered a significant 9-2 defeat against the trio of Justin Rose, Sahith Theegala, and Tommy Fleetwood.

Reflecting on the outcome, Woods candidly admitted, “We got our a** kicked at the end,” visibly frustrated after missing a short putt earlier in the match. Despite the setback, the evening was a blend of personal connections and the unyielding spirit of competition.

Vanessa Trump and Tiger Woods were pictured sharing a romantic moment on Tuesday night

Trump watched as her boyfriend got his ‘a** kicked’ on his long-awaited return to golf action

The golf legend’s girlfriend and daughter Kai (pictured here on Monday) were in the crowd

‘We got our a** kicked at the end,’ said Woods, who earlier missed one short putt and then failed to hide his frustration. 

‘It felt great to be back here with these guys… it was a great team, I’m frustrated that we didn’t get it done.’ 

He added: ‘It feels good to be back but I’d have liked it to be in better circumstances. But that’s the way sports is – you put yourself out there, sometimes you win, sometimes you lose. And you deal with it.’ 

Woods has not played in a PGA Tour event since the 2024 Open Championship. He then underwent yet another back surgery before playing in TGL in early 2025. But Woods’ hopes of a comeback were dashed when he tore his Achilles. 

That sidelined the 15-time major champion for the rest of 2025. Woods then had disk replacement surgery in October. 

He has teased a return at next month’s Masters at Augusta National and Tuesday’s TGL match represented a huge step forward for the golf legend. 

Woods later addressed The Masters. He would not confirm whether or not he will play at Augusta, insisting only: ‘I’ve been trying. It’s just this body doesn’t recover like when I was 24, 25. It doesn’t mean I’m not trying – I’ve been trying for a while. 

‘I’ve had a couple of back injuries the past year that I’ve had to fight through and it’s taken some time. But I keep trying. 

Serena Williams – who co-owns a team with members of her family – was also in the stands

Woods has still not played in a PGA Tour event since the 2024 Open Championship

‘I want to play, I’ve loved the tournament, I’ve loved being there since I was 19 years old. So it’s meant a lot to me and my family over the years and I’m going to be there either way.’ 

When asked if he will leave it until the days leading up to the first round to decide, Woods added: ‘I don’t know, we’ll see how it goes. I’ll be practicing playing at home this week and keep trying to make progress.’

His life off the course has also come under the spotlight in recent months after reports emerged that Vanessa feels ‘insecure’ about their romance.

The golfer and Trump, 48, the ex-wife Donald Trump Jr., went public with their relationship last March, and were recently spotted cozying up to one another at the Genesis Invitational at Riviera Country Club in greater Los Angeles.

However, reports claim Woods, who split from his ex-wife Elin Nordegren 2010 amid cheating allegations, reportedly feels stifled in his relationship with Trump.

‘She’s insecure when it comes to him and other women,’ a source told the National Enquirer. ‘So Vanessa follows Tiger everywhere and checks up on him and what he’s up to through mutual friends when they’re not together.’ 

‘Tiger’s feeling henpecked and stifled,’ they added. ‘He wants Vanessa to trust him and not judge him on prior behavior. But the more serious they get, the more fearful she becomes that Tiger will slide into bad habits and self-sabotage.’ 

Trump has been by Woods’ side at a number of high-profile appearances over the past few months, including the 15-time major winner’s lavish 50th birthday bash in January.