Rian Robertson’s four-game winning streak came to an end in a tense fifth appearance on Jeopardy!, leaving the Ottawa software developer just short of a spot in the Tournament of Champions.

Robertson entered Wednesday, October 7, with $64,101 in winnings and faced two strong challengers: editor John Edwards of Brooklyn, New York, and library support coordinator Anne Damtoft of Silver Spring, Maryland.

Robertson fights back in the first round

The returning champion had a difficult start, but managed to climb out of the red before finding the first Daily Double on clue 10.

With $1,000 on the board, Robertson wagered everything on a clue from the “Travel Writing” category. The clue referenced John Steinbeck’s Travels With Charley and described a West Coast landmark as “the great arch hung from filaments.”

Robertson correctly identified the answer as the Golden Gate Bridge, doubling his score to $2,000 and moving into second place.

When the first round ended, Edwards held the lead with $5,600, followed by Robertson at $3,600 and Damtoft at $3,000.

Edwards takes control in Double Jeopardy

The momentum shifted dramatically in the second round.

Damtoft found the first Daily Double on the opening clue. With $3,000, she wagered it all on “Say the Word.” The clue asked for the word describing a daring fighter that originated from the sound of a sword striking a shield.

Her answer, “swashbuckler,” was correct, putting her in first place with $6,000.

Later, Edwards found the final Daily Double. He had already built a sizeable advantage with $12,800, compared with Damtoft’s $6,800, and chose to risk $6,000 on a clue from “Lampoons and Such.”

The clue described TCM’s characterization of Airplane! as a “takeoff” on films such as Zero Hour! Edwards gave the correct response, increasing his score to $18,800.

“Very impressive,” Ken Jennings told him.

By the end of Double Jeopardy, Edwards had extended his lead to $20,400. Damtoft followed with $15,600, while Robertson entered Final Jeopardy in third with $6,800.

All three contestants solve Final Jeopardy

The final category was “Television.”

The clue asked which series, debuting in 1998, featured a main love interest inspired by Ronald Galotti, a publisher for Vogue and Vanity Fair during the 1990s.

All three contestants came up with the correct response: Sex and the City.

Robertson wagered $4,001, finishing with $10,801. Damtoft added $4,801 to reach $20,401, while Edwards risked $10,801 and finished with $31,201.

That was enough to give Edwards the victory and end Robertson’s run after four consecutive wins. Edwards will return for his second game on Thursday, while Robertson did not qualify for the Tournament of Champions.

Robertson opens up about the challenge of multiple games

After the episode, Robertson took to Reddit to discuss the demanding experience of filming multiple games in a single day.

He asked former champion Justin Robbins whether he had also felt mentally scrambled by his third game, noting that he had experienced the same feeling and wondered whether the third game might be the toughest part of a taping day.

Robbins said he had experienced some of that difficulty, although he attributed his own struggles more to a challenging Double Jeopardy round and a particularly fast buzzer opponent. He also pointed out that Robertson had already played twice before reaching that point in the taping day, something that could make the experience especially draining.

Robertson had previously spoken about just how demanding the Jeopardy! taping schedule can be. Five episodes can be recorded in a day, with returning champions sometimes having only five to 10 minutes to change shirts before heading back to the stage. He described the process as “mentally gruelling” and said the experience gave him a greater appreciation for why contestants can appear to lose momentum after several games.

Despite the fifth-game loss, Robertson leaves his run with four victories and $64,101 in winnings. His appearance also made him the latest returning champion to demonstrate just how quickly the physical and mental demands of multiple Jeopardy! games can add up.

Jeopardy! airs weekdays; check local listings for times. Episodes stream the following day on Hulu and Peacock.