Owen OBrien highlighted Landen Roupp as a pitcher to back due to a favorable matchup against the slumping Phillies offense. Roupp is coming off a strong outing versus the Reds, allowing just one run over six innings. He showed promise in his rookie campaign last year (3.58 ERA across mixed roles), finishing strong with no runs allowed in two of his last three starts. Meanwhile, the Phillies were shut out twice and only managed four total runs in their weekend series against the Cardinals, giving Roupp increased viability as a bet in Monday's matchup and attractive DFS appeal.

Sean Zerillo recommended backing Giants pitcher Landen Roupp against Philadelphia, forecasting San Francisco should be road favorites instead of current slight underdogs. Roupp impressively diversified his pitch mix, reducing curveball reliance (from 44% to 29%) in favor of increased changeups (9.4% to 18.9%) and a newly-added cutter (7%). Although stuff grades on these new offerings remain average (changeup: 87 Stuff+, cutter: 80 Stuff+), his sinker (100 Stuff+) and curve (109 Stuff+) grades are strong. Roupp maintains an exceptional career ground-ball rate consistently above 50%, providing a reliably high floor. Conversely, Taijuan Walker's command issues persist despite improved velocity and Stuff+. Walker's called-strike plus whiff (CSW%) rate and botERA currently sit at six-year lows, suggesting continuing underlying issues even though superficial indicators have improved from his disastrous 2024 season. Zerillo emphasized Roupp's clear pitching advantage, projecting San Francisco's first five innings moneyline value up to -105 and full-game moneyline to +102.

Chris Bennett suggests Landen Roupp as an inexpensive pitching option ($7,300), highlighting his strong strikeout ability demonstrated by eight strikeouts in just four innings in his previous start. Roupp faces a Cincinnati Reds lineup that's striking out at a notable 23.6% rate and posting a low 79 wRC+ against right-handed pitchers. Bennett cautioned about winds blowing out in San Francisco, but still saw value in Roupp's potential upside relative to his cost.

ESPN Fantasy recommended Landen Roupp as a strong streaming option as he faces the Cincinnati Reds at pitcher-friendly Oracle Park. Roupp earned the final spot in the Giants rotation over Hayden Birdsong, who recently pitched four scoreless innings in relief. Despite mixed results in Roupp's first start—fanning eight but walking four and lasting only four innings at Houston—this matchup is favorable due to the Reds' league-low 6.2% walk rate, increasing Roupp's chance of pitching deep into the game.